Dean had his first hit, "Bumming Around", in 1953[3] on the 4 Star label (written by Pete Graves, credited to "C. Graves" on the Quality label). Dean signed with Columbia Records in 1957.
He had minor pop hits, such as "Little Sandy Sleighfoot" (a Christmas novelty song) and "Sing Along", later used as the theme for TV's Sing Along with Mitch, hosted by chorus leader Mitch Miller.
In 1954, Dean hosted the popular Washington, D.C., radio program Town and Country Time on WARL-AM, and with his Texas Wildcats became popular in the Mid-Atlantic region.[3] Patsy Cline and Roy Clark got their starts on the show. Although Cline and Dean became good friends, Clark (Dean's lead guitarist) was fired by the singer for what was explained as his chronic tardiness. Dean replaced Clark with Billy Grammer. In 1955, Town and Country Time moved to WMAL-TV (now WJLA-TV) on weekday afternoons.[3] Dean and the Texas Wildcats also appeared during 1957 on Town and Country Jamboree on WMAL-TV on Saturdays, which was also carried by TV stations in neighboring Maryland and Virginia on a regional network.
Also during 1957, while he lived in Arlington, Virginia, Dean hosted Country Style on WTOP-TV (now WUSA-TV). CBS picked up the show nationally from Washington for eight months in 1957 under the name The Morning Show.[5][6] Then from September 14, 1958, to June 1959, CBS carried The Jimmy Dean Show on weekday and Saturday afternoons.[3]
Dean became best known for "Big Bad John", his 1961 recitation song about a heroic miner.[3] Recorded in Nashville, the record went to number one on the Billboard pop chart and inspired many imitations and parodies.[3] It sold over one million copies and was awarded a gold disc.[7] The track peaked at number two in the UK Singles Chart.[8] The song won Dean the 1962 Grammy Award for Best Country & Western Recording.[3] He had several more top 40 songs, including a top 10 in 1962 with "PT-109", a song in honor of President John F. Kennedy's bravery in World War II,[3] with the sinking of his PT-boat in the South Pacific Ocean by the Japanese.
In the early 1960s, he hosted The Tonight Show on occasion (he was the first guest host during Johnny Carson's tenure, hosting for the first time on January 14, 1963) and one night introduced country singer Roy Clark, with whom he had remained friendly. In the mid-1960s, Dean helped bring country music into the mainstream[9] with his 1963–66 variety series The Jimmy Dean Show. It presented country music entertainers including Roger Miller, George Jones, Charlie Rich, Buck Owens, and some (such as Joe Maphis) who seldom received network exposure. In 1964, he hosted Hank Williams Jr. in Williams' first television appearance at the age of 14. He sang several songs associated with his father, Hank Williams.[10] The program also featured comedy and a variety of popular music artists, and Dean's sketches with Rowlf the Dog, one of Jim Henson's Muppets. Henson was so grateful for this break that he offered Dean a 40% interest in his production company, but Dean declined on the basis that he had done nothing to truly earn it and Henson deserved all the rewards for his own work. For the rest of his life, Dean made it clear that he never regretted this decision.[11]
Dean appeared on several TV talk shows and game shows in the 1960s and performed on variety programs, including The Ed Sullivan Show, The Pat Boone Chevy Showroom and The Hollywood Palace.[12] Dean turned to acting after his television series ended in 1966. His best-known role was as a reclusive Las Vegas billionaire Willard Whyte, inspired by Howard Hughes, in the James Bond movie Diamonds Are Forever (1971) with Sean Connery as Bond. He also appeared in 14 episodes of Daniel Boone (1967–70) in three different roles (one episode as "Delo Jones," two as "Jeremiah," and 11 as "Josh Clements"); as Charlie Rowlands in two Fantasy Island episodes (1981–82); and on other television shows including a semi-regular role as Charlie Bullets on J.J. Starbuck starring Dale Robertson (1987–1988).[12]
Dean's singing career remained strong into the mid-1960s; in 1965, he achieved a second number one country hit with the ballad "The First Thing Ev'ry Morning (And the Last Thing Ev'ry Night)",[3] and he had a top 40 hit that year with "Harvest of Sunshine". In 1966, Dean signed with RCA Victor and immediately had a top 10 hit with "Stand Beside Me".[3] His other major hits during this time included "Sweet Misery" (1967) and "A Thing Called Love" (1968).[3] He continued charting into the early 1970s with his major hits, including "Slowly" (1971), a duet with Dottie West,[3] and a solo hit with "The One You Say Good Morning To" (1972).[13]
In 1976, Dean achieved a million-seller with another recitation song called "I.O.U.", a tribute to his mother and mothers everywhere.[3] The song was released a few weeks before Mother's Day and quickly became a top 10 country hit, his first in 10 years, and a top 40 pop hit, his first in 14 years. The song was re-released in 1977, 1983, and 1984, but with minor success each time.
In January 1978, Dean hosted an all-star tribute to Elvis Presley titled Nashville Remembers Elvis on His Birthday, during which he reminisced about his friendship with the recently deceased singer and performed his own hit "Big Bad John" and "Peace in the Valley".
In 1969, he founded the Jimmy Dean Sausage Company[1] with his brother Don. The company did well in part because of Dean's own extemporized, humorous commercials.[14]
The success of the company led to its acquisition in 1984 by Consolidated Foods, later renamed the Sara Lee Corporation. Dean remained involved as spokesman for the company, but the new corporate parent immediately began phasing him out of any management duties. In January 2004, Dean said that Sara Lee had dropped him as the spokesman for the sausage brand because he was too old.[15] In March 2004, Dean revealed that he had sold all but one of his shares in Sara Lee stock.[16] In 2018, several years after his death, the sausage company began re-airing some classic commercials featuring the voice of Dean introducing himself and praising the product.[2]