Kline made his film debut in Sophie's Choice (1982) before winning the Academy Award for Best Supporting Actor for his comedic role in A Fish Called Wanda (1988).

He also acted in The Pirates of Penzance (1983), Silverado (1985), Cry Freedom (1987), The January Man (1989), Soapdish (1991), Grand Canyon (1991), Chaplin (1992), Dave (1993), The Ice Storm (1997), In & Out (1997), The Emperor's Club (2002), A Prairie Home Companion (2006), and Beauty and the Beast (2017).

He received nomination for the Primetime Emmy Award for Outstanding Lead Actor in a Limited or Movie for playing the title role in the PBS production of Cyrano de Bergerac (2008).

[13][citation needed] The Company traveled across the U.S. performing Shakespeare's plays, other classical works, and the musical The Robber Bridegroom, founding one of the most widely praised groups in American repertory theatre.

[14] In 1976, Kline left The Acting Company and settled in New York City, doing a brief appearance as Woody Reed in the now-defunct soap opera Search for Tomorrow.

[2] In 1978, he played Bruce Granit, a matinée idol caricature, in Harold Prince's On the Twentieth Century, for which he won his first Tony Award.

In 1981, he appeared with multi-genre renowned singer Linda Ronstadt and singer Rex Smith in the New York Shakespeare Festival's Central Park production of Gilbert and Sullivan's The Pirates of Penzance, which moved to Broadway and won Kline another Tony Award for Best Leading Actor in a Musical for his comically dashing portrayal of the Pirate King.

[2] In 1983 he played the role in a film version of the musical, also with Ronstadt, Smith and Angela Lansbury, which had a limited theatrical release.

Kline was dubbed "the American Olivier" by New York Times theater critic Frank Rich for his stage acting.

He reunited with Kasdan with the western film Silverado (1985) where he starred with Kevin Costner, Rosanna Arquette, and John Cleese.

Newsday critic Lynn Darling wrote on July 13, 1988, that Kline "has proved himself to be one of the most talented and versatile American actors of his generation."

In 1993, Kline had his first voice-acting role in The Nutcracker, and starred in Dave, a political comedy directed by Ivan Reitman and co-starring Charles Grodin, Sigourney Weaver and Ben Kingsley.

The film ended its theatrical run on October 10, 1999 after five months, having grossed $113,804,681 domestically and $108,300,000 overseas for a worldwide total of $222,104,681 against a production budget of $170 million.

Kline voiced Tulio in the DreamWorks animated film The Road to El Dorado (2000) opposite Kenneth Branagh's Miguel.

Kline starred alongside Meryl Streep, Lily Tomlin, Tommy Lee Jones, and Woody Harrelson.

[27] He also appeared in a Lincoln Center production that combined the two parts of Henry IV on Broadway at the Vivian Beaumont Theatre in 2003 as Falstaff, and was nominated for the 2004 Tony Award for Actor in a Play.

In January 2008, Kline won a Screen Actors Guild award for his portrayal of Jaques in Kenneth Branagh's film As You Like It, adapted from Shakespeare's play.

That year, he also played Maurice in the musical live-action adaptation of Disney's Beauty and the Beast, directed by Bill Condon and co-starring with Emma Watson and Dan Stevens.

[35][36][37] He also voiced Calvin Fischoeder in the animated comedy series Bob's Burgers (2011–present), for which he earned a Primetime Emmy nomination.

[40] The Kevin Kline Awards honor theatre professionals in St. Louis in an array of categories, including best actor and actress, set design, choreography, and new play or musical.