This is an album page with an inscribed, hand-signed paper applied from comedian, vaudevillian, radio, television and film actor, Jack Benny.

SIZE: The outer dimensions of the album page are about 6" x 4.5"

DATE: Circa 1935

CONDITION: Generally clean condition.

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From Wikipedia on Benny:

Jack Benny (born Benjamin Kubelsky; February 14, 1894 – December 26, 1974) was an American comedian, vaudevillian, radio, television and film actor, and violinist. Recognized as a leading 20th-century American entertainer, Benny often portrayed his character as a miser, who obliviously played his violin badly, and ridiculously claimed to be 39 years of age, regardless of his actual age.

Benny was known for his comic timing and the ability to cause laughter with a pregnant pause or a single expression, such as his signature exasperated "Well!" His radio and television programs, popular from 1932 until his death in 1974, were a major influence on the sitcom genre. Benny was born Benjamin Kubelsky in Chicago on February 14, 1894, and grew up in nearby Waukegan. He was the son of Jewish immigrants Meyer Kubelsky (1864–1946) and Emma Sachs Kubelsky (1869–1917), sometimes called "Naomi." Meyer was a saloon owner and later a haberdasher who had emigrated to America from Poland.

Emma had emigrated from Lithuania. Benny began studying violin, an instrument that became his trademark, at the age of 6, his parents hoping for him to become a professional violinist. He loved the instrument, but hated practice. His music teacher was Otto Graham Sr., a neighbor and father of Otto Graham of NFL fame. At 14, Benny was playing in dance bands and his high school orchestra. He was a dreamer and poor at his studies, and was ultimately expelled from high school. He later did poorly in business school and at attempts to join his father's business. In 1911, he began playing the violin in local vaudeville theaters for $7.50 a week, equal to $205.79 today. He was joined on the circuit by Ned Miller, a young composer and singer.

That same year, Benny was playing in the same theater as the young Marx Brothers. Minnie, their mother, enjoyed Benny's violin playing and invited him to accompany her boys in their act. Benny's parents refused to let their son go on the road at 17, but it was the beginning of his long friendship with the Marx Brothers, especially Zeppo Marx. The next year, Benny formed a vaudeville musical duo with pianist Cora Folsom Salisbury, a buxom 45-year-old divorcée who needed a partner for her act. This angered famous violinist Jan Kubelik, who feared that the young vaudevillian with a similar name would damage his reputation. Under legal pressure, Benjamin Kubelsky agreed to change his name to Ben K. Benny, sometimes spelled Bennie. When Salisbury left the act, Benny found a new pianist, Lyman Woods, and renamed the act "From Grand Opera to Ragtime." They worked together for five years and slowly integrated comedy elements into the show. They reached the Palace Theater, the "Mecca of Vaudeville," and did not do well. Benny left show business briefly in 1917 to join the United States Navy during World War I, and often entertained the sailors with his violin playing. One evening, his violin performance was booed by the sailors, so with prompting from fellow sailor and actor Pat O'Brien, he ad-libbed his way out of the jam and left them laughing. He received more comedy spots in the revues and did well, earning a reputation as a comedian and musician.

Shortly after the war, Benny developed a one-man act, "Ben K. Benny: Fiddle Funology". He then received legal pressure from Ben Bernie, a "patter-and-fiddle" performer, regarding his name, so he adopted the sailor's nickname of Jack. By 1921, the fiddle was more of a prop, and the low-key comedy took over.

Benny had some romantic encounters, including one with dancer Mary Kelly, whose devoutly Catholic family forced her to turn down his proposal because he was Jewish. Benny was introduced to Kelly by Gracie Allen. Some years after their split, Kelly resurfaced as a dowdy fat girl and Jack gave her a part in an act of three girls: one homely, one fat, and one who couldn't sing.

In 1922, Benny accompanied Zeppo Marx to a Passover seder in Vancouver at the residence where he met 17-year-old Sadie Marks (whose family was friends with, but not related to, the Marx family). Their first meeting did not go well when he tried to leave during Sadie's violin performance. They met again in 1926. Jack had not remembered their earlier meeting and instantly fell for her. They married the following year. She was working in the hosiery section of the Hollywood Boulevard branch of the May Company, where Benny courted her. Called on to fill in for the "dumb girl" part in a Benny routine, Sadie proved to be a natural comedienne. Adopting the stage name Mary Livingstone, Sadie collaborated with Benny throughout most of his career. They later adopted a daughter, Joan (b. 1934). Her older sister Babe would be often the target of jokes about unattractive or masculine women, while her younger brother Hillard would later produce Benny's radio and TV work.

In 1929 Benny's agent, Sam Lyons, convinced Irving Thalberg, American film producer at Metro-Goldwyn-Mayer, to watch Benny at the Orpheum Theatre in Los Angeles. Benny signed a five-year contract with MGM, where his first role was in The Hollywood Revue of 1929. The next movie, Chasing Rainbows, did not do well, and after several months Benny was released from his contract and returned to Broadway in Earl Carroll's Vanities. At first dubious about the viability of radio, Benny grew eager to break into the new medium. In 1932, after a four-week nightclub run, he was invited onto Ed Sullivan's radio program, uttering his first radio spiel "This is Jack Benny talking. There will be a slight pause while you say, 'Who cares?'..."

Benny had been a minor vaudeville performer before becoming a national figure with The Jack Benny Program, a weekly radio show that ran from 1932 to 1948 on NBC and from 1949 to 1955 on CBS. It was among the most highly rated programs during its run.

Benny's long radio career began on April 6, 1932, when the NBC Commercial Program Department auditioned him for the N. W. Ayer & Son agency and their client, Canada Dry, after which Bertha Brainard, head of the division, said, "We think Mr. Benny is excellent for radio and, while the audition was unassisted as far as orchestra was concerned, we believe he would make a great bet for an air program." Recalling the experience in 1956, Benny said Ed Sullivan had invited him to guest on his program (1932), and "the agency for Canada Dry ginger ale heard me and offered me a job."

With Canada Dry ginger ale as a sponsor, Benny came to radio on The Canada Dry Program, on May 2, 1932, broadcast on Mondays and Wednesdays on the NBC Blue Network, featuring George Olsen and his orchestra. After a few shows, Benny hired Harry Conn as writer. The Mary Livingstone character was introduced as a fan and aspiring comedian on the July 27 broadcast. The show continued on Blue for six months until October 26, moving to CBS on October 30, now airing Thursdays and Sundays. With Ted Weems leading the band, Benny stayed on CBS until January 26, 1933,[13] when Canada Dry opted not to renew Benny's contract after it attempted to replace Conn with Sid Silvers, who would have also gotten a co-starring role. Unlike later incarnations of the Benny show, The Canada Dry Program was primarily a musical program.

Benny then appeared on The Chevrolet Program, airing on the NBC Red Network between March 17, 1933 until April 1, 1934, initially airing on Fridays (replacing Al Jolson), moving to Sunday nights in the fall. The show, which featured Benny and Livingstone alongside Frank Black's orchestra and vocalists James Melton and (later) Frank Parker, ended after General Motors' president insisted on a musical program.

He continued with sponsor General Tire on Fridays through the end of September, with Don Bestor replacing Black as bandleader. It was with General Tire when Don Wilson became the show's announcer, actually being the tenth one in the show's history (among his predecessors were Ed Thorgerson and Jimmy Wallington).

In October, 1934, General Foods agreed to take up sponsorship from the struggling tire-maker, using the show (now airing on the Blue network) to promote its low-selling Jell-O desserts. Beginning from this point, Benny was heard Sunday evenings at 7, at the time seen as a "graveyard slot". However, this would be eventually associated with Benny, who would appear in that very time spot for his remaining 21 years on radio (counting his TV shows, he would broadcast on Sundays for a record 28 consecutive years). In the fall of 1935, Bestor was replaced by Johnny Green as the maestro, while Parker would be replaced by Michael Bartlett, who himself left after 13 weeks, with Kenny Baker taking over. In early 1936, Harry Conn left the program after creative conflicts with Benny, who had to resort to vaudeville writers Al Boasberg and Edmund Beloin through the end of the season.

The 1936-37 season brought many changes instrumental to the development of the show. Aside from having a new writing team (Beloin and Bill Morrow, with script doctoring by Boasberg), Benny returned to the NBC Red Network and established the program in Hollywood. Benny had already done a number of shows on the Coast for two years—featuring Jimmie Grier as guest conductor—whenever he was doing movie work. Green was replaced by Phil Harris. During this period, the Benny character gradually became that of the vain, miserly, untalented performer he would be recognized for, while the "ditzy" role went from Mary to Kenny and Don Wilson would become the target of jokes about his weight. Halfway through the season, the famous "feud" with Fred Allen began, climaxing with a visit to New York, after which Eddie Anderson was cast as a porter. His character was so well received that it was decided to have Anderson join the cast as Rochester, Benny's valet. In 1939, Baker was replaced by Dennis Day.

In 1941, NBC celebrated Benny's tenth anniversary in radio in an unprecedented manner, broadcasting part of a banquet dedicated to him, in which the network conceded the Sunday 7 to 7.30 pm slot to Benny instead of the sponsor, as it was the custom during the Golden Age of Radio.

In 1942, General Foods switched the sponsor product from Jell-O to Grape-Nuts. World War II affected the show as Harris joined the Merchant Marines, being absent from the program from December 1942 until March 1943. That fall, Bill Morrow joined the Army and Beloin left, being both replaced by Milt Josefsberg, John Tackaberry, George Balzer and Cy Howard, the latter of which would be soon replaced by Sam Perrin. Day enlisted in the Navy in early 1944, not returning until 1946. The new writers emphasized sitcom situations instead of the film parodies prevalent in earlier years.

After 10 years with General Foods, American Tobacco's Lucky Strike became Benny's sponsor from October 1944, an association that lasted until 1959.

The show switched networks to CBS on January 2, 1949, as part of CBS president William S. Paley's notorious "raid" on NBC talent in 1948–49. It stayed there for the remainder of its radio run, ending on May 22, 1955. In 1952, Harris was replaced by Bob Crosby. CBS aired repeat episodes from 1956 to 1958 as The Best of Benny.

The Jack Benny Program evolved from a variety show blending sketch comedy and musical interludes into the situation comedy form we now recognize, crafting particular situations and scenarios from the fictionalization of Benny the radio star. Common situations included hosting parties, income tax time, nights on the town, "backstage" interactions between Jack and his cast at the radio studio during show rehearsals, contract negotiations, or traveling by train or plane to and from Jack's many personal appearances throughout the country (hence the "Train leaving on track five" gag). The writers and star would insert musical interludes from Phil Harris and Dennis Day. With Day, invariably, a brief sketch ended with Benny ordering Day to sing the song he planned for the show that week.

One popular scenario that became a tradition on The Jack Benny Program was the annual "Christmas Shopping" episode, in which Benny would go to a local department store to do his shopping. Each year, Benny would buy a ridiculously cheap Christmas gift for Don Wilson, from a harried store clerk played by Mel Blanc. Benny would then drive Blanc to insanity by exchanging the gift countless times throughout the episode.

In the 1946 Christmas episode, for example, Benny buys shoelaces for Don, and is unable to make up his mind whether to give Wilson shoelaces with plastic tips or metal tips. After exchanging them repeatedly, Mel Blanc is heard screaming insanely, "Plastic tips! Metal tips! I can't stand it anymore!" A variation in 1948 was with an expensive wallet, but repeatedly changing the greeting card, prompting Blanc to shout, "I haven't run into anyone like you in 20 years! Oh, why did the governor have to give me that pardon!?" Benny then realizes that he should have gotten Don a wallet for $1.98, whereupon the store clerk responds by committing suicide. Over the years, in the Christmas episodes, Benny bought and repeatedly exchanged cuff links, golf tees, a box of dates, a paint set (water colors or oils), and a gopher trap. In later years, Benny would encounter Mel Blanc's wife (played by Jean Vander Pyl) or the clerk's psychiatrist at the store, and drive them crazy as well.

In 1936, after a few years of broadcasting from New York, Benny moved the show to Los Angeles, allowing him to bring in guests from among his show business friends, including Frank Sinatra, James Stewart, Judy Garland, Barbara Stanwyck, Bing Crosby, Burns and Allen (George Burns was Benny's closest friend), and many others. Burns, Allen and Orson Welles guest hosted several episodes in March and April 1943 when Benny was ill with pneumonia, while Ronald Colman and his wife Benita Hume appeared often in the 1940s as Benny's long-suffering neighbors.

On the broadcast of January 8, 1950, journalist Drew Pearson was the subject of a joke gone wrong. Announcer Don Wilson was supposed to say he heard that Jack bought a new suit on Drew Pearson, but said the name wrong; Don said "Drear Pewson". Later in the show, comedic actor Frank Nelson was asked by Benny if he was the doorman.

Changing his original response at the suggestion of the writers, Nelson said, "Well, who do you think I am, Drear Pewson?" The audience laughed for almost 30 seconds.

In the 1960s Benny was the headlining act at Harrah’s Lake Tahoe with performer Harry James, and Vocalist Ray Vasquez.

In the early days of radio and in the early television era, airtime was owned by the sponsor, and Benny incorporated the commercials into the body of the show. Sometimes the sponsors were the butt of jokes, though Benny did not use this device as frequently as his friend and "rival" Fred Allen did then, or as cast member Phil Harris later did on his successful radio sitcom. Nevertheless, for years, Benny insisted in contract negotiations that his writers pen the sponsor's commercial in the middle of the program (leaving the sponsor to provide the opening and closing spots) and the resulting ads were cleverly and wittily worked into the storyline of the show. For example, on one program, Don Wilson accidentally misread Lucky Strike's slogan ("Be happy, go Lucky") as "Be Lucky, go happy", prompting a story arc over several weeks that had Wilson unable to appear on the show due to being traumatized by the error.

In fact, the radio show was generally not announced as The Jack Benny Program. Instead, the primary name of the show tied to the sponsor. Benny's first sponsor was Canada Dry Ginger Ale from 1932 to 1933. Benny's sponsors included Chevrolet from 1933 to 1934, General Tire in 1934, and Jell-O from 1934 to 1942. The Jell-O Program Starring Jack Benny was so successful in selling Jell-O, in fact, that General Foods could not manufacture it quickly enough when sugar shortages arose in the early years of World War II, and the company stopped advertising the popular dessert mix. General Foods switched the Benny program from Jell-O to Grape-Nuts from 1942 to 1944, and it was, naturally, The Grape Nuts Program Starring Jack Benny. Benny's longest-running sponsor, was the American Tobacco Company's Lucky Strike cigarettes, from 1944 to 1955, when the show was usually announced as The Lucky Strike Program starring Jack Benny.

Benny was notable for employing a small group of writers, most of whom stayed with him for many years. This was in contrast to successful radio or television comedians, such as Bob Hope, who would change writers frequently. One of Benny's writers, George Balzer, noted: "One of the nice things about writing for Jack Benny was that he never denied your existence. On the contrary, he publicized it—not just in conversations, but in interviews and on the air." Historical accounts (like those by longtime Benny writer Milt Josefsberg) indicate that Benny's role was essentially as head writer and director of his radio programs, though he was not credited in either capacity. In contrast to Fred Allen, who initially wrote his own radio scripts (and extensively rewrote scripts produced in later years by a writing staff), Jack Benny was often described by his writers as a consummate comedy editor rather than a writer per se. George Burns described Benny as "the greatest editor of material in the business. He's got the knack of cutting out all the weak slush and keeping in only the strong, punchy lines."

Jack Benny has a reputation as a master of timing. Since his days in radio, he often explored the limits of timing for comedic purposes, like pausing a disproportionate amount of time before answering a question. Balzer described writing material for Benny as similar to composing music, with one element being the rhythm of delivery as equivalent to musical tempo.

During his early radio shows, there was no recurring theme, the program instead opening each week with a different then-current popular song. Throughout the Jello and Grapenuts years, announcer Don Wilson would announce the name of the show, some of the cast, then state "The orchestra opens the program with [name of song]." The orchestra number would continue softly as background for Don Wilson's opening commercial.

Starting in the Lucky Strike era, Benny adopted a medley of "Yankee Doodle Dandy" and "Love in Bloom" as his theme music, opening every show. "Love in Bloom" was later the theme of his television show. His radio shows often ended with the orchestra playing "Hooray for Hollywood". The TV show ended with one of two bouncy instrumentals written for the show by his musical arranger and conductor, Mahlon Merrick.

Benny would sometimes joke about the propriety of "Love in Bloom" as his theme song. On a segment often played in Tonight Show retrospectives, Benny talks with Johnny Carson about this. Benny says he has no objections to the song in and of itself, only as his theme. Proving his point, he begins reciting the lyrics slowly and deliberately: "Can it be the trees. That fill the breeze. With rare and magic perfume. Now what the hell has that got to do with me?"

In 1937, Benny began his famous radio feud with rival Fred Allen. Allen kicked the feud off on his own show on December 30, 1936, after child violinist Stuart Canin gave a performance of François Schubert's The Bee[2]:131 credibly enough that Allen wisecracked about "a certain alleged violinist" who should by comparison be ashamed of himself. Benny, who listened to the Allen show, answered in kind at the end of his January 3, 1937, show. And the two comedians were off and running.

For a decade, the two went at it back and forth, so convincingly that fans of either show could have been forgiven for believing they had become blood enemies. In reality, the two men were close friends and mutual admirers. Benny and Allen often appeared on each other's show during the ongoing feud; numerous surviving episodes of both comedians' radio shows feature each other, in both acknowledged guest spots and occasional cameos. On one Christmas program Allen thanked Benny for sending him a Christmas tree, but then added that the tree had died. "Well, what do you expect," quipped Allen, "when the tree is in Brooklyn and the sap is in Hollywood."

Benny in his eventual memoir (Sunday Nights at Seven) and Allen in his Treadmill to Oblivion later revealed that each comedian's writing staff often met together to plot future takes on the mock feud. If Allen zapped Benny with a satirization of Benny's show ("The Pinch Penny Program"), Benny shot back with a parody of Allen's Town Hall Tonight called "Clown Hall Tonight." And their playful sniping ("Benny was born ignorant, and he's been losing ground ever since") was also advanced in the films Love Thy Neighbor and It's in the Bag!.

Perhaps the climax of the feud came during Fred Allen's parody of popular quiz-and-prize show Queen for a Day, which was barely a year old when Allen decided to have a crack at it on The Fred Allen Show—an episode that has survived for today's listeners to appreciate. Calling the sketch "King for a Day", Allen played the host and Benny a contestant who sneaked onto the show using the alias Myron Proudfoot. Benny answered the prize-winning question correctly and Allen crowned him "king" and showered him with a passel of almost meaningless prizes. Allen proudly announced, "Tomorrow night, in your ermine robe, you will be whisked by bicycle to Orange, New Jersey, where you will be the judge in a chicken-cleaning contest," to which Benny joyously declared, "I'm king for a day!" At this point a professional pressing-iron was wheeled on stage, to press Benny's suit properly. It didn't matter that Benny was still in the suit. Allen instructed his aides to remove Benny's suit, one item at a time, ending with his trousers, each garment's removal provoking louder laughter from the studio audience. As his trousers began to come off, Benny howled, "Allen, you haven't seen the end of me!" At once Allen shot back, "It won't be long now!"

The laughter was so loud and chaotic at the chain of events that the Allen show announcer, Kenny Delmar, was cut off the air while trying to read a final commercial and the show's credits. (Allen was notorious for running overtime often enough, largely thanks to his ad-libbing talent, and he overran the clock again this time.)

Benny was profoundly shaken by Allen's sudden death from a heart attack in 1956. In a statement released on the day after Allen's death, Benny said, "People have often asked me if Fred Allen and I were really friends in real life. My answer is always the same: You couldn't have such a long-running and successful feud as we did, without having a deep and sincere friendship at the heart of it." Allen himself wrote, "For years people have been asking me if Jack and I are friendly. I don't think that Jack Benny has an enemy in the world. ... He is my favourite comedian and I hope to be his friend until he is forty. That will be forever."

After making his television debut in 1949 on local Los Angeles station KTTV,[20] then a CBS affiliate, the network television version of The Jack Benny Program ran from October 28, 1950, to 1965, all but the last season on CBS. Initially scheduled as a series of five "specials" during the 1950–1951 season, the show appeared every six weeks for the 1951–1952 season, every four weeks for the 1952–1953 season and every three weeks in 1953–1954. For the 1953–1954 season, half the episodes were live and half were filmed during the summer, to allow Benny to continue doing his radio show. From the fall of 1954 to 1960, it appeared every other week, and from 1960 to 1965 it was seen weekly.

On March 28, 1954, Benny co-hosted General Foods 25th Anniversary Show: A Salute to Rodgers and Hammerstein with Groucho Marx and Mary Martin. In September 1954, CBS premiered Chrysler's Shower of Stars co-hosted by Jack Benny and William Lundigan. It enjoyed a successful run from 1954 until 1958. Both television shows often overlapped the radio show. In fact, the radio show alluded frequently to its television counterparts. Often as not, Benny would sign off the radio show in such circumstances with the line "Well, good night, folks. I'll see you on television."

When Benny moved to television, audiences learned that his verbal talent was matched by his controlled repertory of dead-pan facial expressions and gesture. The program was similar to the radio show (several of the radio scripts were recycled for television, as was somewhat common with other radio shows that moved to television), but with the addition of visual gags. Lucky Strike was the sponsor. Benny did his opening and closing monologues before a live audience, which he regarded as essential to timing of the material. As in other TV comedy shows, a laugh track was added to "sweeten" the soundtrack, as when the studio audience missed some close-up comedy because of cameras or microphones obstructing their view. Television viewers became accustomed to live without Mary Livingstone, who was afflicted by a striking case of stage fright that didn't lessen even after performing with Benny for 20 years. Hence, Livingstone appeared rarely if at all on the television show. In fact, for the last few years of the radio show, she pre-recorded her lines and Jack and Mary's daughter, Joan, stood in for the live taping, with Mary's lines later edited into the tape replacing Joan's before broadcast. Mary Livingstone finally retired from show business permanently in 1958, as her friend Gracie Allen had done.

Benny's television program relied more on guest stars and less on his regulars than his radio program. In fact, the only radio cast members who appeared regularly on the television program as well were Don Wilson and Eddie Anderson. Day appeared sporadically, and Harris had left the radio program in 1952, although he did make a guest appearance on the television show (Bob Crosby, Phil's "replacement", frequently appeared on television through 1956). A frequent guest was the Canadian-born singer-violinist Gisele Mackenzie. As a gag, Benny made a 1957 appearance on the then-wildly popular $64,000 Question. His category of choice was "Violins", but after answering the first question correctly Benny opted out of continuing, leaving the show with just $64; host Hal March gave Benny the prize money out of his own pocket. March made an appearance on Benny's show the same year.

Benny was able to attract guests who rarely, if ever, appeared on television. In 1953, both Marilyn Monroe and Humphrey Bogart made their television debuts on Benny's program. Another guest star on the Jack Benny show was Rod Serling who starred in a spoof of The Twilight Zone in which Benny goes to his own house..and finds that no one knows who he is!

Canadian singer Gisele MacKenzie, who toured with Benny in the early 1950s, guest starred seven times on The Jack Benny Program. Benny was so impressed with MacKenzie's talents that he served as co-executive producer and guest starred on her 1957–1958 NBC variety show, The Gisele MacKenzie Show.

In 1964, Walt Disney was a guest, primarily to promote his production of Mary Poppins. Benny persuaded Disney to give him over 110 free admission tickets to Disneyland for his friends and one for his wife, but later in the show Disney apparently sent his pet tiger after Benny as revenge, at which point Benny opened his umbrella and soared above the stage like Mary Poppins.

In due course the ratings game finally got to Benny, too. CBS dropped the show in 1964, citing Benny's lack of appeal to the younger demographic the network began courting, and he went to NBC, his original network, in the fall, only to be out-rated by CBS's Gomer Pyle, U.S.M.C. The network dropped Benny at the end of the season. He continued to make occasional specials into the 1970s, the last one airing in January 1974.

In his unpublished autobiography, I Always Had Shoes (portions of which were later incorporated by Jack's daughter, Joan Benny, into her memoir of her parents, Sunday Nights at Seven), Benny said that he, not NBC, made the decision to end his TV series in 1965. He said that while the ratings were still very good (he cited a figure of some 18 million viewers per week, although he qualified that figure by saying he never believed the ratings services were doing anything more than guessing, no matter what they promised), advertisers were complaining that commercial time on his show was costing nearly twice as much as what they paid for most other shows, and he had grown tired of what was called the "rate race". Thus, after some three decades on radio and television in a weekly program, Jack Benny went out on top. In fairness, Benny himself shared Fred Allen's ambivalence about television, though not quite to Allen's extent. "By my second year in television, I saw that the camera was a man-eating monster ... It gave a performer close-up exposure that, week after week, threatened his existence as an interesting entertainer."

In a joint appearance with Phil Silvers on Dick Cavett's show, Benny recalled that he had advised Silvers not to appear on television. However, Silvers ignored Benny's advice and proceeded to win several Emmy awards as Sergeant Bilko on the popular series The Phil Silvers Show, while Benny claimed he never won any of the television honors.

Benny also acted in films, including the Academy Award-winning The Hollywood Revue of 1929, Broadway Melody of 1936 (as a benign nemesis for Eleanor Powell and Robert Taylor), George Washington Slept Here (1942), and notably, Charley's Aunt (1941) and To Be or Not to Be (1942). He and Livingstone also appeared in Ed Sullivan's Mr. Broadway (1933) as themselves. Benny often parodied contemporary movies and movie genres on the radio program, and the 1940 film Buck Benny Rides Again features all the main radio characters in a funny Western parody adapted from program skits. The failure of one cinematic Benny vehicle, The Horn Blows at Midnight, became a running gag on his radio and television programs, although contemporary viewers may not find the film as disappointing as the jokes suggest. Benny may have had an unbilled cameo role in Casablanca, claimed by a contemporary newspaper article and advertisement and reportedly in the Casablanca press book. When asked in his column "Movie Answer Man", movie critic Roger Ebert first replied, "It looks something like him. That's all I can say." He wrote in a later column, "I think you're right." Benny also was caricatured in several Warner Brothers cartoons including Daffy Duck and the Dinosaur (1939, as Casper the Caveman), I Love to Singa, Slap Happy Pappy, and Goofy Groceries (1936, 1940, and 1941 respectively, as Jack Bunny), Malibu Beach Party (1940, as himself), and The Mouse that Jack Built (1959). The last of these is probably the most memorable: Robert McKimson engaged Benny and his actual cast (Mary Livingstone, Eddie Anderson, and Don Wilson) to do the voices for the mouse versions of their characters, with Mel Blanc—the usual Warner Brothers cartoon voicemeister—reprising his old vocal turn as the always-aging Maxwell, always a phat-phat-bang! away from collapse. In the cartoon, Benny and Livingstone agree to spend their anniversary at the Kit-Kat Club, which they discover the hard way is inside the mouth of a live cat. Before the cat can devour the mice, Benny himself awakens from his dream, then shakes his head, smiles wryly, and mutters, "Imagine, me and Mary as little mice." Then, he glances toward the cat lying on a throw rug in a corner and sees his and Livingstone's cartoon alter egos scampering out of the cat's mouth. The cartoon ends with a classic Benny look of befuddlement. It was rumored that Benny requested that, in lieu of monetary compensation, he receive a copy of the finished film.

Benny made a cameo appearance in It's A Mad, Mad, Mad, Mad World. When some of the characters are arguing at the side of the road, Benny pulls up in his car and considerately asks, "Trouble? Having any trouble?", to which the character played by Ethel Merman yells, "Yes, and we don't need any help from you!" Benny does a take with his smile slowly fading and mutters, "Well!", and drives off.

Benny teamed with Fred Allen for the best-remembered running gag in classic radio history, in terms of character dialogue. But Benny alone sustained a classic repertoire of running gags in his own right, including his skinflint radio and television persona; regular cast members' and guest stars' reference to his "baby blue" eyes, always sure to elicit a self-satisfied smirk or patently false attempt at modesty from Benny; perpetually giving his age as 39; and ineptitude at violin playing, most frequently demonstrated by futile attempts to perform Rodolphe Kreutzer's Étude No. 2 in C major. In fact, Benny was a fairly good violinist who achieved the illusion of a bad one, not by deliberately playing poorly, but by striving to play pieces that were too difficult for his skill level. In one of his show's skits, Benny is a USO performer in the Pacific when playing his violin when he comes under fire; Benny still plays his violin when two Japanese surrender to him–all the other enemy soldiers committed suicide rather than endure listening to Benny's terrible music!

A skit heard numerous times on radio, and seen many times on television, had Mel Blanc as a Mexican in a sombrero and serape sitting on a bench. Jack Benny sits down and begins a conversation. To each question asked by Benny, Blanc replies Sí. When Benny asks his name, Blanc replies Sy, which would prompt the exchange, Sy?, Sí. And when Benny asks where Blanc is going, Blanc replies, "to see his sister", Sue (Sue?, Sí.), who of course sews for a living (Sew?, Sí.).

A running gag in Benny's private life concerned George Burns. To Benny's eternal frustration, he could never get Burns to laugh. Burns, on the other hand, could crack Benny up with the least effort. An example of this occurred at a party when Benny pulled out a match to light a cigar. Burns announced to all, "Jack Benny will now perform the famous match trick!" Benny had no idea what Burns was talking about, so he proceeded to light up. Burns observed, "Oh, a new ending!" and Benny collapsed in helpless laughter. Benny even had a sound-based running gag of his own: his famous basement vault alarm, allegedly installed by Spike Jones, ringing off with a shattering cacophony of whistles, sirens, bells and blasts before ending invariably with the sound of a foghorn. The alarm rang even when Benny opened his safe with the correct combination. The vault also featured a guard named Ed (voiced by Joseph Kearns) who had been on post down below before, apparently, the end of the Civil War, the end of the Revolutionary War, the founding of Los Angeles, on Jack's 38th birthday and even the beginning of humanity. In one appearance, Ed asked Benny, "By the way, Mr. Benny ... what's it like on the outside?" Benny responded, "... winter is nearly here, and the leaves are falling." Ed responded, "Hey, that must be exciting," to which Benny replied (in a stunningly risqué joke for the period), "Oh, no—people are wearing clothes now." In one episode of the Benny radio show, Ed the Guard actually agreed when Benny invited him to take a break and come back to the surface world, only to discover that modern conveniences and transportation, which hadn't been around the last time he'd been to the surface, terrorized and confused him. (Ed thought a crosstown bus was "a red and yellow dragon".) Finally, Ed decides to return to his post fathoms below and stay there. The basement vault gag was also used in the cartoon The Mouse that Jack Built and an episode of The Lucy Show.

A separate sound gag involved a song Benny had written, "When You Say I Beg Your Pardon, Then I'll Come Back to You". Its inane lyrics and insipid melody guaranteed that it would never be published or recorded, but Benny continued to try to con, extort or otherwise inveigle some of his musical guests (including The Smothers Brothers and Peter, Paul and Mary) to perform it. However, none ever made it all the way.

In keeping with his "stingy" schtick, on one of his television specials he remarked that, to his way of looking at things, a "special" is when the price of coffee is marked down. Another popular running gag concerned the social habits of Benny's on-air orchestra, who were consistently portrayed as a bunch of drunken ne'er-do-wells. Led first by Phil Harris and later by Bob Crosby, the orchestra, and in particular band member Frank Remley, were jokingly portrayed as often being too drunk to play properly, using an overturned bass drum to play cards on just minutes before a show and so enamored of liquor that the sight of a glass of milk would make them sick. Remley was portrayed in various unflattering situations, such as being thrown into a garbage can by a road sweeper who had found him passed out in the street at 4 a.m., and on a wanted poster at the Beverly Hills police station.

One Christmas program had Crosby agonizing over what to get Remley:

Benny: "Well, why don't you get him a cordial; like a bottle of Drambuie?" Crosby: "That's a nice thought, Jack, but Drambuie's an after-dinner drink." Benny: "So?" Crosby: "So Remley never quite makes it 'til after dinner."

Crosby also got consistent laughs by frequently joking about his more famous brother Bing Crosby's vast wealth.

Starting with the October 24, 1937 radio show, when Jack proudly announced the purchase of his car, a running joke began that Benny drove an old Maxwell automobile, a brand that went out of business in 1925. Although some details such as the car's body style and its exact model year would vary over the years, what remained constant was that Benny's old car was so worn out that it would barely run, but the miserly Benny insisted he could get a few more miles out of it. Many of the sound effects for the car's clattering engine came from an actual old motor that the sound effects shop had salvaged from a Los Angeles junkyard. When a sound effects man missed a cue for the automobile engine, Mel Blanc quickly improvised a vocal imitation of a sputtering car engine starting up noisily that was so funny it became a regular feature of the show. The ongoing saga of the Maxwell was initially interrupted after just five years, when on the October 18, 1942 broadcast Jack took his car to a local junkyard and contributed it to the World War II junk salvage drive, receiving $7.50 in war stamps in exchange. However, much of the radio audience may have remained unaware that the Maxwell was ever gone, because before long Benny was heard traveling around in a decrepit old car again, and by the end of the 1940s his car would once more be specifically identified as a Maxwell. When the Jack Benny Program premiered on television in 1950, a 1916 Maxwell Model 25 Tourer became one of the production's standard props. Benny's Maxwell later became a 1923 Tourer. Benny would often make public appearances in Maxwells. He drove a Maxwell onto the stage in one of his last television specials.

By 1941, Jack Benny's Maxwell had become such a well-known aspect of popular culture that it was referenced in the Billy Mills song "I'm in Love with the Sound Effects Man" as heard on the June 17, 1941 Fibber McGee and Molly radio show (and later performed on a 1943 recording by Spike Jones). The automobile was also featured in the 1943 Benny film The Meanest Man in the World. Benny and his archaic auto were featured in a series of television and print ads for Texaco from the 1950s through the 1970s. A series of gags was built around the premise that Benny appreciated the value of Sky Chief brand gasoline in keeping his car running smoothly, but was too cheap to buy more than one gallon at a time. In the classic cartoon "The Mouse that Jack Built", Benny and his wife are driven by Rochester in a sputtering Maxwell car.

Many people believe that Benny appears behind the wheel of his Maxwell in the 1963 film It's a Mad, Mad, Mad, Mad World, but in fact it was a 1932 Cadillac. The long shots for the scene were shot months before Benny was cast—with a stunt driver at the wheel—and the role was intended for Stan Laurel (which is why the character wears a derby, which Benny almost never did). When Laurel ultimately passed on appearing, Jack agreed to play the role. According to the commentary on the Criterion edition of the film, his close-ups were filmed on a rear-projection stage at the Paramount studio.

After his broadcasting career ended, Benny performed live as a standup comedian and returned to films in 1963 with a cameo appearance in It's a Mad, Mad, Mad, Mad World. Benny made one of his final television appearances July 20, 1973 on The Tonight Show Starring Johnny Carson. Benny was preparing to star in the film version of Neil Simon's The Sunshine Boys when his health failed in 1974. He prevailed upon his longtime best friend, George Burns, to take his place on a nightclub tour while preparing for the film. Burns ultimately had to replace Benny in the film as well and went on to win an Academy Award for his performance.

Despite his failing health, Benny made several appearances on The Dean Martin Celebrity Roast in his final 18 months, roasting Ronald Reagan, Johnny Carson, Bob Hope and Lucille Ball, in addition to himself being roasted in February 1974. The Lucille Ball roast, his last public performance, aired on February 7, 1975, several weeks after his death.

In October 1974, Benny cancelled a performance in Dallas after suffering a dizzy spell, coupled with numbness in his arms. Despite a battery of tests, Benny's ailment could not be determined. When he complained of stomach pains in early December, a first test showed nothing, but a subsequent examination showed that he had inoperable pancreatic cancer. Benny went into a coma at home on December 22, 1974. While in a coma, he was visited by close friends including George Burns, Bob Hope, Frank Sinatra, Johnny Carson, John Rowles and then Governor Ronald Reagan. He died on December 26, 1974 at age 80. At the funeral, Burns, Benny's best friend for more than fifty years, attempted to deliver a eulogy but broke down shortly after he began and was unable to continue. Hope also delivered a eulogy in which he stated, "For a man who was the undisputed master of comedic timing, you would have to say this is the only time when Jack Benny's timing was all wrong. He left us much too soon." Benny was interred in a crypt at Hillside Memorial Park Cemetery in Culver City, California. His will arranged for a single long-stemmed red rose to be delivered to his widow, Mary Livingstone, every day for the rest of her life. Livingstone died nine years later on June 30, 1983.

In trying to explain his successful life, Benny summed it up by stating: "Everything good that happened to me happened by accident. I was not filled with ambition nor fired by a drive toward a clear-cut goal. I never knew exactly where I was going."

Upon his death, Benny's family donated his personal, professional and business papers, as well as a collection of his television shows, to UCLA. The university established the Jack Benny Award for Comedy in his honor in 1977 to recognize outstanding people in the field of comedy. Johnny Carson was the first award recipient. Benny also donated a Stradivarius violin (purchased in 1957) to the Los Angeles Philharmonic Orchestra. Benny had commented, "If it isn't a $30,000 Strad, I'm out $120."

In 1960, Benny was inducted into the Hollywood Walk of Fame with three stars. His stars for television and motion pictures are located at 6370 and 6650 Hollywood Boulevard, respectively, and at 1505 Vine Street for radio. He was inducted into the Television Hall of Fame in 1988 and the National Radio Hall of Fame in 1989. He was also inducted into the Broadcasting and Cable Hall of Fame.

Benny was inducted as a laureate of The Lincoln Academy of Illinois and awarded the Order of Lincoln (the state's highest honor) by the governor of Illinois in 1972 in the area of the performing arts.

When the price of a standard first-class U.S. postal stamp was increased to 39 cents in 2006, fans petitioned for a Jack Benny stamp to honor his stage persona's perpetual age. The U.S. Postal Service had issued a stamp depicting Benny in 1991 as part of a booklet of stamps honoring comedians; however, the stamp was issued at the then-current rate of 29 cents.

Jack Benny Middle School in Waukegan is named after Benny. Its motto matches his famous statement as "Home of the '39ers". A statue of Benny with his violin now stands on Genesee Street in downtown Waukegan.

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