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Robert Dennis Crumb (; born August 30, 1943) is an American cartoonist and musician who often signs his work R. Crumb. His work displays a nostalgia for American folk culture of the late 19th and early 20th centuries, and satire of contemporary American culture. Crumb is a prolific artist and contributed to many of the seminal works of the underground comix movement in the 1960s, including being a founder of the first successful underground comix publication, Zap Comix, contributing to all 16 issues. He was additionally contributing to the East Village Other and many other publications, including a variety of one-off and anthology comics.
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 (b. 1965).  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.
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Did he develop any other characters early on?

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Hartman was born Philip Edward Hartmann (later dropping one "n") on September 24, 1948, in Brantford, Ontario, Canada. He was the fourth of eight children of Doris Marguerite (Wardell) and Rupert Loebig Hartmann, a salesman specializing in building materials. His parents were Catholic and raised their children in that faith. As a child Hartman found affection hard to earn and stated: "I suppose I didn't get what I wanted out of my family life, so I started seeking love and attention elsewhere."
Working alone as a graphic artist, Hartman frequently amused himself with "flights of voice fantasies". Citing the need for a more social outlet for his talents, Hartman, aged 27, began in 1975 to attend evening comedy classes run by the California-based improvisational comedy group The Groundlings. While watching one of the troupe's performances, Hartman impulsively decided to climb on stage and join the cast. After several years of training, paying his way by re-designing the group's logo and merchandise, Hartman formally joined the cast of The Groundlings; by 1979 he had become one of the show's stars.  Hartman met comedian Paul Reubens and the two became friends, often collaborating on writing and comedic material. Together they created the character Pee-wee Herman and developed The Pee-wee Herman Show, a stage performance which also aired on HBO in 1981. Hartman played Captain Carl on The Pee-wee Herman Show and returned in the role for the children's show Pee-wee's Playhouse. Reubens and Hartman made cameos in the 1980 film Cheech & Chong's Next Movie. Hartman co-wrote the script of the 1985 feature film Pee-wee's Big Adventure and had a cameo role as a reporter in the film. Although he had considered quitting acting at the age of 36 due to limited opportunities, the success of Pee-wee's Big Adventure brought new possibilities and changed his mind. After a creative falling-out with Reubens, Hartman left the Pee-Wee Herman project to pursue other roles.  In addition to his work with Reubens, Hartman recorded a number of voice-over roles. These included appearances on The Smurfs, Challenge of the GoBots, The 13 Ghosts of Scooby-Doo, and voicing characters Henry Mitchell and George Wilson on Dennis the Menace. Additionally Hartman developed a strong persona providing voice-overs for advertisements.
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Did they do any shows together in his early career?

Answer:
Together they created the character Pee-wee Herman and developed The Pee-wee Herman Show, a stage performance which also aired on HBO in 1981.