Bean was born Dallas Frederick Burrows in Burlington, Vermont, the son of Marian Ainsworth (née Pollard) and George Frederick Burrows. His father was a founding member of the American Civil Liberties Union (ACLU), a fund-raiser for the Scottsboro Boys' defense, and a 20-year member of the campus police of Harvard College. Orson graduated from the Cambridge Rindge and Latin School. He is a first cousin twice removed of Calvin Coolidge, who was President of the United States at the time of Bean's birth. Orson Bean is a founding member of The Sons of the Desert, the international Laurel and Hardy Society. Bean served for 18 months (1946-1947) in the United States Army stationed in Japan, where he worked on his magic act.
Following this, he worked in small venues as a stage magician. He then transitioned to standup comedy, changing his name by combining a pompous first name (Orson Welles) with a silly last name.
In 1952, Bean made a guest appearance on NBC Radio's weekly hot-jazz series The Chamber Music Society of Lower Basin Street. His vocal mannerisms were ideal for the mock-serious tone of the show, and he became the show's master of ceremonies ("Dr. Orson Bean") for its final season. Bean was a frequent guest on The Tonight Show (with both Jack Paar and Johnny Carson), and appeared on game shows originating from New York. He was a regular panelist on To Tell the Truth in versions from the late 1950s through 1991. On July 5th, 1965 his father appeared as a subject of the panel and he had to disqualify himself from participating. Apparently no one knew his real name was Burrows as Kitty Carlisle humorously admitted in her questioning. He appeared on Super Password and Match Game, among other game shows. He hosted a pilot for a revamped version of Concentration in 1985 which was picked up later on in 1987 as Classic Concentration with Alex Trebek.
He played the title character in the 1960 Twilight Zone episode "Mr. Bevis". In 1961, for the CBS anthology series The DuPont Show with June Allyson, he starred as John Monroe in "The Secret Life of James Thurber", based on the works of the American humorist James Thurber.
On Broadway, he was the star of the original cast of Will Success Spoil Rock Hunter? (1955), and was featured in Subways Are For Sleeping (1961), for which he received a Tony Award nomination as Best Featured Actor in a Musical, as well as Never Too Late (1962). He also starred in Illya Darling, the 1967 musical adaptation of the film Never on Sunday. In 1964 he produced the Obie Award winning Home Movies and appeared on Broadway in I Was Dancing.
He was a regular on both Mary Hartman, Mary Hartman and its spin-off, Fernwood 2Nite, and also played the shrewd businessman and storekeeper Loren Bray on the television series Dr. Quinn, Medicine Woman throughout its six-year run on CBS in the 1990s. He played John Goodman's homophobic father on the sitcom Normal, Ohio. He played the main characters Bilbo and Frodo Baggins in the 1977 and 1980 Rankin/Bass animated adaptations of J.R.R. Tolkien's The Hobbit, and The Return of the King. He also played Dr. Lester in Spike Jonze's 1999 film, Being John Malkovich. Bean appeared in the last two episodes of Season 7 of 2003 in 7th Heaven as a patient. In 2005, Bean appeared in the sitcom Two and a Half Men, in an episode entitled "Does This Smell Funny to You?", playing a former playboy whose conquests included actresses Tuesday Weld and Anne Francis. He appeared in the 2007 How I Met Your Mother episode "Slapsgiving" as Robin Scherbatsky's 41-year-old boyfriend, Bob. In 2009, he was cast in the recurring role of Roy Bender, a steak salesman, who is Karen McCluskey's love interest on the ABC series Desperate Housewives. And in 2016, at age 87, Bean appeared in the American TV sitcom Modern Family, in an episode entitled "Playdates".
Bean wrote an autobiographical account about his life-changing experience with the orgone therapy developed by Austrian-born psychoanalyst Wilhelm Reich (1897–1957). It was entitled Me and the Orgone: The True Story of One Man's Sexual Awakening (1971).
He has been married three times.
His first wife was actress Jacqueline de Sibour (stage name: Rain Winslow), whom he married in 1956 and divorced in 1962. She was the daughter of Vicomte Jacques J. de Sibour, a French nobleman and pilot, and his wife, Violette B. Selfridge (later Mrs. Frederick T. Bedford), daughter of British department-store magnate Harry Gordon Selfridge. Jacqueline and Bean had one child, Michele.
His second wife was fashion designer Carolyn Maxwell. They married in 1965 and divorced in 1981. They had three children: Max, Susannah, and Ezekiel. Susannah was married to conservative commentator Andrew Breitbart until his death; they had four children.
His third wife is actress Alley Mills, 23 years his junior; they married in 1993 and live in Los Angeles.
Bean left the United States and lived in Australia in the 1960s.
Bean was a frequent guest on The Tonight Show Starring Johnny Carson in the 1970s. Since 2008, Bean has been a regular guest on the Dennis Miller radio show, stating that he is a Christian of orthodox beliefs and very thankful for the career success that he has had.Me and the Orgone (1972) ISBN 0-9679670-1-5
Too Much Is Not Enough (1988) ISBN 0-8184-0465-5
25 Ways to Cook a Mouse for the Gourmet Cat (1994) ISBN 1-55972-199-5
M@il for Mikey (2007)
At the Hungry i (1959 Fantasy UFAN 7009), comedy
I Ate the Baloney (1969 Columbia CS 9743), comedy