In 1991, Baldwin met his future wife Kim Basinger on the set of the critically panned The Marrying Man. He appeared with Basinger again in The Getaway, a 1994 remake of the 1972 Steve McQueen film of the same name.

In a brief but memorable role, Baldwin played a ferocious sales executive in 1992's Glengarry Glen Ross, a part added to the film version of David Mamet's Pulitzer Prize-winning stage play. He then chose to star in 1992's Prelude to a Kiss with Meg Ryan, based on the Broadway play, rather than reprise his role as CIA analyst Ryan in another Tom Clancy thriller, Patriot Games. His film was a commercial flop, while Harrison Ford scored back-to-back hits as Ryan.

Baldwin played the title character in another film that failed at the box office, 1994's The Shadow. His late '90s roles also had a lukewarm reception. They included several thrillers, such as The Edge (with Anthony Hopkins), The Juror (with Demi Moore) and Heaven's Prisoners (with Teri Hatcher).

Baldwin then shifted more toward being a character actor, including his Academy Award nominated turn in 2003's gambling drama The Cooler and in working with director Martin Scorsese and Leonardo DiCaprio in The Aviator and The Departed.

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