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Grammer, having trained as an actor at Juilliard and the Old Globe Theatre, made his professional acting debut as Lennox in the 1981 Broadway revival of Macbeth. The following year, he portrayed Cassio acting opposite Christopher Plummer and James Earl Jones in Othello. In mid-1983, he acted alongside Mandy Patinkin in the original off-Broadway production of Stephen Sondheim's musical Sunday in the Park with George. He has since starred in the leading roles in productions of Sweeney Todd: The Demon Barber of Fleet Street, My Fair Lady, Big Fish, and Finding Neverland.

In film, he is known for his role as Dr. Hank McCoy / Beast in the superhero films X-Men: The Last Stand (2006), X-Men: Days of Future Past (2014) and The Marvels (2023). His other roles include Down Periscope (1996), The Pentagon Wars (1998), and Swing Vote (2008). He is also known for his voice roles in Anastasia (1997), Toy Story 2 (1999), and as Sideshow Bob in The Simpsons (1990–present). He took guest roles in the sitcoms 30 Rock (2010–2012), Unbreakable Kimmy Schmidt (2016), and Modern Family (2017). For his performance as the corrupt mayor in the Starz political series Boss (2011–2012), he received a Golden Globe Award for Best Actor – Television Series Drama.

In early 2010, Grammer returned to Broadway in the musical revival of La Cage aux Folles, where he received a nomination for the Tony Award for Best Leading Actor in a Musical. In mid-2016, Grammer won a Tony Award for Best Musical as producer of a musical revival of The Color Purple. In early 2019, he starred as Don Quixote in a production of Man of La Mancha at the London Coliseum. In late 2023, The Telegraph described Grammer as one of "the finest actors" of his generation. He was awarded a star on the Hollywood Walk of Fame on May 22, 2001.