Born in San Francisco, he studied at the Mark Hopkins Art Institute for six months, started his career as an unpaid cartoonist for The San Francisco Examiner.[4] The Honolulu Advertiser was among the other newspapers art departments that he served in.[5] He also contributed to the San Francisco Evening Post. He also worked as an itinerant actor (for both stage and screen), newspaper illustrator, and piano player.[3] In 1906 he moved to the East Coast. In the 1910s he contributed many illustrations to both Red Book magazine and its sister publication, Green Book.[4]

Before World War I, Irvin contributed illustrations regularly to Life, and rose to the position of art editor. (Life the humorous weekly, and not to be confused with the more famous magazine of the same name published by Henry Luce). Irvin also contributed to Cosmopolitan when it was a serious literary publication. He illustrated Wallace Irwin's "Letters of a Japanese Schoolboy" in Life.[6] He would later incorporate Japanese imagery in satirical kakemono for The New Yorker.[6]

He also created a series of humorous advertisements for Murad (turkish tobacco cigarettes).[6]

He also contributed the illustrations for "Snoot If You Must," by Lucius Beebe, a noted raconteur of New York's cafe society (1943, D. Appleton-Century).

He was fired from his position as art editor at Life in 1924.

However, Irvin had joined an advisory board to help launch The New Yorker and then worked on the magazine's staff as an illustrator and art editor. When he had first taken the job, Irvin had assumed that the magazine would fold after a few issues,[4] but his work would ultimately appear on the cover of 169 issues of The New Yorker between 1925 and 1958.[7]

The magazine's first cover, of a dandy peering at a butterfly through a monocle, was drawn by Irvin; the dandy replaced at the last minute a drawing of theater curtains revealing the skyline of Manhattan.[3] The gentleman on the original cover is referred to as "Eustace Tilley," a character created for The New Yorker by Corey Ford. Another example is the piece known as The Unity of the Allied Nations, which appeared on the cover of the July 1, 1944 issue, and depicts the national personifications of the Allies (the American Eagle, the Chinese Dragon, the Russian Bear and the British Lion).[7]

Besides covers for the magazine, Irvin also drew various illustrations, department headings, caricatures, and cartoons.[3]

The New Yorker signature display typeface, used for its nameplate and headlines and the masthead above The Talk of the Town section, is called "Irvin" or "Irvin type," after him.[8] An alphabet drawn by the American etcher Allen Lewis, who had received training in woodcutting in Paris, was used as the typographical basis for the "Irvin type."[3] Irvin may have spotted Lewis' lettering, which was drawn to imitate a woodcut, in a pamphlet entitled "Journeys To Bagdad", and liked it so much that Irvin asked Lewis to create the entire alphabet.[3] Uninterested in this project, Lewis suggested that Irvin create the alphabet himself –this became the "Irvin type."[3]

Eustace Tilley is a caricature that appeared on the cover of the first issue of The New Yorker in 1925 and has appeared on the cover in various forms of every anniversary issue of the magazine except 2017. He was not initially named, but acquired the name from Corey Ford in subsequent issues as part of a fictional magazine history backstory included to fill the early issues of the magazine. The original cover was drawn by Rea Irvin, but a younger and more modern looking version of him as drawn by Johan Bull in subsequent months appeared throughout the magazine in its early years. This later version was given the name Tilley and subsequently the original cover was also declared to be Tilley. Because of the cover's prominence, almost all of the references to Tilley in the press discuss the Irvin version.

Until 1994, the original cover artwork was reproduced for the annual anniversary edition, but, since then, there has been significant variation in how his character has been embodied. He has become the mascot of the magazine and is described as a dandy. There have been two years without any anniversary issue and in other years when the anniversary celebration/remembrance has broken from previously-established tradition it has resulted in stories in publications such as The Washington Post and The New York Times. Since 2008, artist have competed in an annual Eustace Tilley contest with prizes that include the potential to have their artistic interpretation submissions chosen for the anniversary cover. All contest submissions are derived from Irvin's version.

Tilley was born out of necessity when the coverless first edition of The New Yorker was set to print. After editor-in-chief and founder Harold Ross was unsatisfied by the array of artist submissions under the theme of "a curtain going up on Manhattan", Ross turned to art editor Rea Irvin with the directive to produce a cover that "would make the subscribers feel that we’ve been in business for years and know our way around".[1] Irvin was The New Yorker's first employee and its de facto art editor. He drew the magazine's first cover of the character, modelling him on caricature of the Count d'Orsay in the December 1834 edition of Fraser's Magazine.[2] This caricature can be found under the subject "costume" in the 11th edition of the Encyclopædia Britannica published in 1910 ("Costume", Encyclopædia Britannica, eleventh edition, vol. 7 (New York: Encyclopædia Britannica Co., 1910), 244, fig. 47.).[3] Irvin, who had 4 months earlier drawn a magazine cover of well-clad gentleman, added features to the 19th century stylistic source image: a monocle to represent erudite intellect as well as a butterfly for "whimsey".[1]

Since advertisers were not filling the pages of the unfamiliar magazine at first, it commissioned Corey Ford to fill the pages with a series of humor pieces that "pretended to provide an inside look at the making of the magazine" with illustrations of the mascot, in which he was dubbed with the name Eustace Tilley. His appearances in the series is likened thematically to Where's Wally?/Where's Waldo?.[4] Tilley was presented as the hero of Ford's series which was titled "The Making of a Magazine". He was introduced inside front cover of the August 8, 1925 issue with a more youthful appearance than that of the original cover art subject. Ford combined the last name of a somewhat humorous aunt of his with the name Eustace due to euphony. His top hat was of a newer style, without the curved brim. He wore a morning coat and striped formal trousers.[5] The series ran for 21 chapters of pseudo-intellectual parody and first presented Tilley in close-up in Chapter XVII.[1] The range of activities and duties held by Tilley within the magazine in the decades after "The Making of a Magazine" gave a reputation as a man of action on top of his erudite man of taste presentation.[6] For the "The Making of a Magazine" chapters, Tilley was drawn with modern attire of the day by Johan Bull (whose tenure with the magazine seems to have ended in 1927), although each feature's layout was ornamented with Irvin's 19th century-cladded version at the top.[1] At some point well after Tilley was named on the inside we are told that he is the same named person in the original cover art that would be reused annually.[1] In Chapter XX, we are told that Eustace was born to Mrs. Terwilliger Tilley on January 1, 1876.[1]

Ross believed Tilley was the highlight of the inaugural issue and each year that the magazine managed to survive, he acknowledge this by putting him on the cover again.[1] By appearing on the cover exactly as originally drawn every year for decades on the issue closest to the anniversary date of February 21, Tilley has become a kind of mascot for The New Yorker. He has frequently made appearance within the magazine and on promotional materials, with occasional artistic license used to provide variation on his appearance. More recent anniversary editions have "parodied, subverted or deconstructed" the original artwork.[7]

The New York Times described him as follows: "The enduring symbol of The New Yorker magazine — the aristocratic, top-hatted Regency dandy, Eustace Tilley, studying a fluttering pale pink butterfly through a monocle".[8] The Comics Journal says his depiction is incongruous: "a seeming sophisticated man-about-town who is so vapidly empty-headed as to find a fluttering insect an object worthy of minute inspection."[1] Crosstown rival magazine, New York describes him as a dandy who has always been somewhat condescending.[9] ABC News describes him as "foppish".[10] The Nieman Foundation for Journalism at Harvard University in their Nieman Reports stated that Tilley portrays the "essence" of the magazine—"a slightly condescending but consummately tasteful arbiter of the larger world" despite the fact that he was derived from a less than smart and jazzy source.[2]

The New York Times noted that 1994 was the first anniversary edition that was celebrated with variation that was a mere resemblance, rather than the exact drawing of the original character. The similarities to the "staid, wing-collared" original that year included a "long neck, the pointy nose, the all-but-concealed eye, even the penciled arch of eyebrow".[8] Twice in the late 1990s there was no anniversary edition.[4]

January 7, 2013 was the deadline for the sixth annual Eustace Tilley contest in which readers submit their own interpretations of the magazine's mascot.[10] This suggests the original annual contest was for the 2008 issue. User submissions for the original contest can be found online at Flickr.[11] 9 winning entries from nearly 300 entries were announced in a published release dated February 4, 2008.[12] The original contest earned coverage by outlets such as Gothamist.[13] The 2008 cover was produced in homage to the ongoing 2008 United States presidential election cycle as a two-headed face card dubbed Eustace Tillarobama, with depictions of Barack Obama and Hillary Clinton.[1] By the time of the sixth annual edition, editors selected 12 winners and readers subsequently voted to determine 5 readers choice winners.[14] When interviewed by New York, 2013 contest winner Simon Greiner described his hipster work on updating of Tilley's physical cues based on the original as follows: "the sideburns into the beard, the monocle into the eyeglasses, the coat, and the hat".[9]

In protest of Executive Order 13769 by Donald Trump, the newly seated President of the United States, Tilley was not depicted on the 2017 anniversary issue, instead appearing two issues later.[15][16] That year's anniversary cover was art from John W. Tomac that was based on the hand and torch of The Statue of Liberty in an effort to stand behind American values that welcomed immigrants in contrast to the values Trump expressed via executive order.[17] The March 7, 2017 cover featured a human observer resembling Vladimir Putin and the usual lepidopteran subject of observation with a Trump–based head to highlight the New Cold War.[18] The work by artist Barry Blitt is titled "Eustace Vladimirovich Tilley".[19]

By the time of the 2021 edition of the Eustace Tilley contest, there had been years in which none of the winners actually appeared on the cover and other years in which multiple covers with depictions of the character by multiple artists were published. The range of variations have been significant. The mascot had twice been manifested by contest winners as a femme-presenting Eustacia (once on an anniversary edition cover and once in the summer). Tilley has also been depicted by contest winners as a youthful punk and a youthful hipster as well as a wide variety of character contexts.[20] The 2023 winner and anniversary cover veteran, Tomac, presented Eustace in canine form.[21]