Inspired by Walt Kelly, Fleischer Brothers animation and others, Crumb and his brothers drew their own comics. His cartooning developed as his older brother Charles pushed him and provided feedback. In 1958 the brothers self-published three issues of Foo in imitation of Harvey Kurtzman’s satirical Humbug and Mad which they sold door-to-door with little success, souring the young Crumb on the comic-book business. At fifteen, Crumb collected classical jazz and blues records from the 1920s to the 1940s. At age 16 he lost his Catholic faith.

Crumb’s father gave him $40 when he left home after high school. His first job, in 1962, was drawing novelty greeting cards for American Greetings in Cleveland, Ohio. He stayed with the company for four years, producing hundreds of cards for the company’s Hi-Brow line; his superiors had him draw in a cuter style that was to leave a footprint on his work throughout his career. In Cleveland he met a group of young bohemians such as Buzzy Linhart, Liz Johnston, and Harvey Pekar. Dissatisfied with greeting card work, he tried to sell cartoons to comic book companies, who showed little interest in his work. In 1965, cartoonist Harvey Kurtzman printed some of Crumb’s work in the humor magazine he edited, Help!. Crumb moved to New York, intending to work with Kurtzman, but Help! ceased publication shortly after. Crumb briefly illustrated bubblegum cards for Topps before returning to Cleveland and American Greetings.

Crumb married Dana Morgan in 1964. Nearly destitute, the couple traveled in Europe, during which Crumb continued to produce work for Kurtzman and American Greetings, and Dana stole food. The relationship was unstable as Crumb frequently went his own way, and he was not close to his son Jesse (1968-2018).

Crumb has been married twice. He first married Dana Morgan in 1964, who gave birth to their son Jesse in 1968. Crumb met cartoonist Aline Kominsky in 1972; their relationship soon turned serious and they began living together (on the same property shared by Dana Crumb). In 1978, Crumb divorced Dana and married Aline, with whom Crumb has frequently collaborated. (Dana died in 2014.) In September 1981 Aline gave birth to Crumb’s second child, Sophie. Robert, Aline, and Sophie moved to a small village near Sauve in southern France in 1991.

In 1965 and 1966 Crumb had a number of Fritz the Cat strips published in the men’s magazine Cavalier. Fritz had appeared in Crumb’s work as early as the late 1950s; he was to become a hipster, scam artist, and bohemian until Crumb abandoned the character in 1969.

Crumb was becoming increasingly uncomfortable with his job and marriage when in June 1965 he began taking LSD, a psychedelic drug that was then still legal. He had both good and bad trips. One bad trip left him in a muddled state for half a year, during which for a time he left Dana; the state ended when the two took a strong dose of the drug together in April 1966. Crumb created a number of his best-known characters during his years of LSD use, including Mr. Natural, Angelfood McSpade, and the Snoid.

In January 1967 Crumb came across two friends in a bar who were about to leave for San Francisco; Crumb was interested in the work of San Francisco-based psychedelic poster artists, and on a whim asked if he could join them. There, he contributed upbeat LSD-inspired countercultural work to underground newspapers. The work was popular, and Crumb was flooded with requests, including to illustrate a full issue of Philadelphia’s Yarrowstalks.

Independent publisher Don Donahue invited Crumb to make a comic book; Crumb drew up two issues of Zap Comix, and Donahue published the first in February 1968 under the publisher name Apex Novelties. Crumb had difficulty at first finding retailers who would stock it, and at first his wife took to selling the first run herself out of a baby carriage.

Crumb met cartoonist S. Clay Wilson, an art school graduate who saw himself as a rebel against middle-class American values and whose comics were violent and grotesque. Wilson’s attitude inspired Crumb to give up the idea of the cartoonist-as-entertainer and to focus on comics as open, uncensored self-expression; in particular, his work soon became sexually explicit, as in the pornographic Snatch he and Wilson produced late in 1968.

Crumb was a prolific cartoonist in the late 1960s and early 1970s; at his peak point of output he produced 320 pages over two years. He produced much of his best-known work then, including his Keep on Truckin’ strip, and strips featuring characters such as the bohemian Fritz the Cat, spiritual guru Mr. Natural, and oversexed African-American stereotype Angelfood McSpade. During this period, he launched a series of solo titles, including Despair, Uneeda (published by Print Mint in 1969 and 1970 respectively), Big Ass Comics, R. Crumb’s Comics and Stories, Motor City Comics (all published by Rip Off Press in 1969), Home Grown Funnies (Kitchen Sink Press, 1971) and Hytone Comix (Apex Novelties, 1971), in addition to founding the pornographic anthologies Jiz and Snatch (both Apex Novelties, 1969).

Between 1974 and 1984, Crumb drew at least 17 album covers for Yazoo Records/Blue Goose Records, including those of the Cheap Suit Serenaders. He also created the revised logo and record label designs of Blue Goose Records that were used from 1974 onward.

In 1978, Crumb allowed his artwork to be used as pictorial rubber stamp designs by Top Drawer Rubber Stamp Company, a collaboration between cartoonist Art Spiegelman, publisher Françoise Mouly. and people living at Quarry Hill Creative Center in Rochester, Vermont. R. Crumb’s imagery proved to be some of the most popular designs produced by this avant-garde pictorial stamp company.

While meditating in 1980 Crumb conceived of a magazine with a lowbrow aesthetic inspired by punk zines, Mad, and men’s magazines of the 1940s and 1950s. From 1981 Crumb edited the first eight issues of the twenty-eight issue run of Weirdo, published by Last Gasp; his contributions and tastes determined the contents of the later issues as well, edited by Peter Bagge until #16, and Aline for the remainder of the run. The magazine featured cartoonists new and old, and had a mixed response; Art Spiegelman, who co-edited the slicker Raw, called it a “piece of shit”, and Crumb’s fumetti was so unpopular that it has never appeared in Crumb collections.

In 1984-1985 Crumb produced a series of illustrations for the tenth anniversary edition of Edward Abbey’s environmental-themed novel The Monkey Wrench Gang, published in 1985 by Dream Garden Press of Salt Lake City. Many of these illustrations also appeared in a 1987 Monkey Wrench Gang calendar, and remain available on T-shirts.

R. Crumb Comix, a theatrical production based on his work and directed by Johnny Simons, was produced in Fort Worth, Texas, in 1986. It was revived at Duke University in 1990, and co-starred Avner Eisenberg and Nicholas de Wolff. The development of the play was supervised by Crumb, who also served as set designer, drawing larger-than-life representations of some of his most famous characters all over the floors and walls of the set.

From 1987 to 2005 Fantagraphics Books published the seventeen-volume Complete Crumb Comics and ten volumes of sketches. Crumb (as “R. Crumb”) contributes regularly to Mineshaft magazine, which, since 2009, has been serializing “Excerpts From R. Crumb’s Dream Diary”.

Crumb has received several accolades for his work, including the Inkpot Award in 1989, a nomination for the Harvey Special Award for Humor in 1990 and the Angoulême Grand Prix in 1999.

The Crumbs moved into a house in southeastern France in 1991, which is said to have been financed by the sale of six Crumb sketchbooks. The Terry Zwigoff-directed Crumb documentary appeared in 1994—a project on which Zwigoff had been working since 1985. The film won several major critical accolades.

In 1992 and 1993, Robert Crumb was involved in a project by Dutch formation The Beau Hunks and provided the cover art for both their albums The Beau Hunks play the original Laurel & Hardy music 1 and 2. He also illustrated the albums’ booklets.

Crumb’s work is also filled with unsavory images of African Americans (such as his recurring character Angelfood McSpade), who are often portrayed as indigenous, tribal, and wearing blackface. (Many other underground comix published in the late 1960s-early 1970s feature similar depictions.) Crumb often utilized African American characters as “tokens,” appearing as re-used tropes such as clowns, tribesmen, athletes, etc. Researcher Edward Shannon interpreted the themes of Crumb’s story containing marginalized Africans in “When the Niggers Take Over America” (published in 1993 in Weirdo) like this: “Crumb … explores both the American Dream and its nightmare reflection; in this … strip all-American white middle class children are depicted as cannibals eager to devour the devalued and dehumanized other.” Crumb has responded to criticism by claiming that he did not invent racist caricatures like Angelfood, but that they were part of the American culture in which he was raised. He sees the character as a criticism of the racist stereotype itself and assumed that the hippie/intellectual audiences who read his work in the late 1960s were not racists and would understand his intentions.

Crumb has released CDs anthologizing old original performances gleaned from collectible 78-rpm phonograph records. His That’s What I Call Sweet Music was released in 1999 and Hot Women: Women Singers from the Torrid Regions in 2009. Chimpin’ the Blues, a collaboration with fellow record collector Jerry Zolten, combines rare recordings with conversation about the music and the musicians, was released in 2013. Crumb drew the cover art for these CDs as well.

Crumb was the leader of the band R. Crumb & His Cheap Suit Serenaders, for which he sang lead vocals, wrote several songs and played banjo and other instruments. Crumb often plays mandolin with Eden and John’s East River String Band and has drawn three covers for them: 2009’s Drunken Barrel House Blues, 2008’s Some Cold Rainy Day, and 2011’s Be Kind To A Man When He’s Down on which he plays mandolin. With Dominique Cravic, he founded “Les Primitifs du Futur”—a French-style band based on musette / folk, jazz and blues—and played on its 2000 album World Musette. He also provided the cover art for this and other albums.

In the 2003 movie American Splendor, Crumb was portrayed by James Urbaniak. Crumb’s wife Aline was quoted as saying she hated the interpretation and never would have married Robert if he was like that.

Crumb has frequently drawn comics about his musical interests in blues, country, bluegrass, cajun, French Bal-musette, jazz, big band and swing music from the 1920s and 1930s, and they also heavily influenced the soundtrack choices for his bandmate Zwigoff’s 1995 Crumb documentary. In 2006, he prepared, compiled and illustrated the book R. Crumb’s Heroes of Blues, Jazz & Country, with accompanying CD, which derived from three series of trading cards originally published in the 1980s.

In 2006, Crumb brought legal action against Amazon.com after their Web site used a version of his widely recognizable “Keep on Truckin'” character. The case was expected to be settled out of court.

R. Crumb’s Sex Obsessions, a collection of his most personally revealing sexually-oriented drawings and comic strips, was released by Taschen Publishing in November 2007. In August 2011, following concerns about his safety, Crumb cancelled plans to visit the Graphic 2011 festival in Sydney, Australia after a tabloid labeled him a “self-confessed sex pervert” in an article headlined “Cult genius or filthy weirdo?”.

In 2009, after four years of work, Crumb produced The Book of Genesis, an unabridged illustrated graphic novel version of the biblical Book of Genesis. In 2016, the Seattle Museum of Art displayed the original drawings for the Book of Genesis as part of an exhibit entitled “Graphic Masters: Dürer, Rembrandt, Hogarth, Goya, Picasso, R. Crumb.”

In 2009, Crumb drew the artwork for a 10-CD anthology of French traditional music compiled by Guillaume Veillet for Frémeaux & Associés. The following year, he created three artworks for Christopher King’s Aimer Et Perdre: To Love And To Lose: Songs, 1917–1934 and, in 2011, he once again played mandolin on an Eden and John’s East River String Band album (Be Kind to a Man When He’s Down) for which he also created the album cover artwork.

In 2012, Crumb appeared in five episodes of John’s Old Time Radio Show talking about old music, sex, aliens and Bigfoot. He also played 78-rpm records from his record room in southern France. He has appeared on the show and recorded at least fourteen one-hour podcasts.

In 2013, Crumb played mandolin with the Eden and John’s East River String Band on their album Take A Look at That Baby and also took part in the accompanying music video.

In January 2015, Crumb was asked to submit a cartoon to the left-wing magazine Libération as a tribute for the Charlie Hebdo shooting. He sent a drawing titled “A Cowardly Cartoonist,” depicting an illustration of the backside of Crumb’s friend Mohamid Bakshi, while referencing the prophet Muhammad, founder of Islam.

In 2017, Crumb’s original cover art for the 1969 Fritz the Cat collection published by Ballantine sold at auction for $717,000, the highest sale price to that point for any piece of American cartoon art.