[1] After first rising to prominence with roles in acclaimed films such as Ship of Fools (1965) and King Rat (1965), he co-starred in the classic drama Who's Afraid of Virginia Woolf?

Through the next decade and a half, Segal consistently starred in notable films across a variety of genres including The Quiller Memorandum (1966), The St. Valentine's Day Massacre (1967), No Way to Treat a Lady (1968), Where's Poppa?

(1970), The Owl and the Pussycat (1970), The Hot Rock (1972), Blume in Love (1973), A Touch of Class (1973), California Split (1974), The Duchess and the Dirtwater Fox (1976), Fun with Dick and Jane (1977), Who Is Killing the Great Chefs of Europe?

[2][3][4] Later in his career, he appeared in supporting roles in films such as Carbon Copy (1981), Stick (1985), Look Who's Talking (1989), For the Boys (1991), The Mirror Has Two Faces (1996), Flirting with Disaster (1996), 2012 (2009), and Love & Other Drugs (2010).

[21] He appeared in Antony and Cleopatra for Joseph Papp and joined an improvisational group called The Premise, which performed at a Bleecker Street coffeehouse[22] and whose ranks included Buck Henry and Theodore J.

[30] The role ultimately earned him the Golden Globe Award for New Star of the Year,[14] alongside Harve Presnell and Chaim Topol.

[31] In 1965, Segal played an egocentric painter in an ensemble cast led by Vivien Leigh and Lee Marvin in Stanley Kramer's acclaimed drama Ship of Fools, which was nominated for the Academy Award for Best Picture.

[32][33] In other notable film appearances, he played a secret service agent on assignment in Berlin in The Quiller Memorandum (1966) (a role originally meant for Charlton Heston[34]), an Algerian paratrooper who becomes a leader of the FLN in Lost Command (1966), and a Cagney-esque gangster in Roger Corman's The St. Valentine's Day Massacre (1967).

Nichols had previously directed Segal in a 1964 Off-Broadway play titled The Knack[36] and cast him again in Woolf after Robert Redford had turned down the role.

[37] In the four-person ensemble piece, Segal played the young faculty member, Nick, alongside Elizabeth Taylor, Richard Burton, and Sandy Dennis.

Segal released the album at a time when he appeared regularly playing banjo on The Tonight Show Starring Johnny Carson.

[15] In the same year, Segal played banjo and sang with The Smothers Brothers when they performed Phil Ochs's "Draft Dodger Rag" on their CBS television show.

[41][42] For over ten years after his success with Woolf, Segal received many notable film roles, often working with major filmmakers and becoming a significant figure in the New Hollywood movement.

[48] In one of his most successful roles, Segal played a philandering husband in Melvin Frank's continental romantic comedy A Touch of Class (1973) opposite Glenda Jackson.

He played a perplexed police detective in No Way to Treat a Lady (1968), a war-weary platoon commander in The Bridge at Remagen (1969), a man laying waste to his marriage in Loving (1970), and a hairdresser-turned-junkie in Born to Win (1971).

[50] The Owl and the Pussycat (1970), a romantic comedy starring Segal and Barbra Streisand and written by his former improv teammate Buck Henry, was particularly popular;[51] and though Segal played against type as a dangerous computer scientist in The Terminal Man (1974), he used his popular appeal as a card shark in The Duchess and the Dirtwater Fox (1976), as a suburbanite-turned-bank robber in Fun with Dick and Jane (1977), as a heroic ride inspector in Rollercoaster (1977), and as a wealthy serial restaurant entrepreneur in Who Is Killing the Great Chefs of Europe?

[53] Segal co-hosted the 48th Academy Awards in 1976, alongside Gene Kelly, Goldie Hawn, Walter Matthau, and Robert Shaw.

He made frequent television appearances with the "Beverly Hills Unlisted Jazz Band", whose members included actor Conrad Janis on trombone, and in 1981 they performed live at Carnegie Hall.

[56] Segal reunited with his Touch of Class co-star Jackson and director Frank in another European-set romantic comedy, Lost and Found (1979), but the film was not a success.

Instead, he began to star more frequently in television films, such as The Deadly Game (1982) for which he received a CableAce Award nomination for best actor in a theatrical or non-musical production,[57] The Cold Room (1984), and The Zany Adventures of Robin Hood (1984).

The show, which also starred David Spade and Laura San Giacomo, among others, and which once aired between iconic sitcoms Friends and Seinfeld, lasted for seven seasons and 148 episodes.

He and Jill Clayburgh cameoed as Jake Gyllenhaal's parents in Love & Other Drugs (2010), reuniting the co-stars 46 years after they first worked together in The Terminal Man.

Additionally, Segal worked more frequently as a voice actor, including a role in the English-language version of Studio Ghibli's The Tale of the Princess Kaguya (2013) and a comedic reprisal of his Who's Afraid of Virginia Woolf?

In other roles, Segal played talent manager Murray Berenson in three episodes of the television series Entourage (2009), guest starred in shows such as Boston Legal, Private Practice, and Pushing Daisies, appeared in comedic short videos such as Chutzpuh, This Is,[65] and starred in the TV Land sitcom Retired at 35 (2011–2012), alongside his Bye Bye Braverman co-star Jessica Walter.

[66][67][68] Segal had another success when he starred in the ABC sitcom The Goldbergs (2013–2021), playing Albert "Pops" Solomon, the eccentric but lovable grandfather of a semi-autobiographical family based on that of series creator Adam F.