Baldwin met his future wife Kim Basinger when they played lovers in the 1991 film The Marrying Man.Next, Baldwin played a ferocious sales executive in Glengarry Glen Ross (1992), a part added to the film version of David Mamet's Pulitzer Prize-winning stage play (including the monologue "Coffee's for closers").Baldwin also received an Emmy nomination for the 1995 television version of the production, in which both he and Jessica Lange reprised their roles, alongside John Goodman and Diane Lane.In 1998, Baldwin played the title role in Macbeth at The Public Theater alongside Angela Bassett and Liev Schreiber in a production directed by George C. In 2004, Baldwin starred in a revival of Broadway's Twentieth Century about a successful and egomaniacal Broadway director (Baldwin), who has transformed a chorus girl (Anne Heche) into a leading lady.Baldwin wrote an episode of Law & Order entitled "Tabloid", which aired in 1998. Barrett Moore, a retired plastic surgeon, in the series Nip/Tuck.He starred as Jack Donaghy on NBC's 30 Rock, which first aired October 2006.
He also guest-starred in the first live episode of the series.
He has played both leading and supporting roles in films such as the horror comedy fantasy film Beetlejuice (1988), as Jack Ryan in the action thriller The Hunt for Red October (1990), the romantic comedy The Marrying Man (1991), the superhero film The Shadow (1994), Thomas and the Magic Railroad (2000), and two films directed by Martin Scorsese: the Howard Hughes biopic The Aviator (2004) and the neo-noir crime drama The Departed (2006).
His performance in the 2003 romantic drama The Cooler garnered him a nomination for the Academy Award for Best Supporting Actor.
In 1988, he appeared in Beetlejuice and Working Girl.
He gained further recognition as a leading man with his role as Jack Ryan in The Hunt for Red October (1990).
He left the Thomas the Tank Engine & Friends series in 2002 on winning the role of Lawrence Quinn in The Cat in the Hat and was replaced by Michael Brandon.