Happy 54th Gary
In the Line of Fire (1993)
This film was directed by Wolfgang Peterson (Das Boot, The NeverEnding Story, Air Force One, etc) and also stars Clint Eastwood, John Malkovich and Rene Russo.
Cole stars as the supervisor to Clint Eastwood's Secret Service agent character, Frank Horrigan.
A Simple Plan (1998)
To be completely honest, I don't remember Gary Cole in this movie but there were a lot of obscure characters in this one. I think he plays an FBI agent in it. Or perhaps it was a person pretending to be in the FBI. Can't remember.
Anyway, it was directed by Sam Raimi (Evil Dead, Spider-Man, etc.) and also stars Bill Paxton, Billy Bob Thorton, and Bridget Fonda.
Office Space (1999)
In the role for which in my mind he will ever be remembered.... Bill Lumbergh, the boss of the main character Peter, played by Ron Livingston.
This film, directed by Mike Judge (King of the Hill, Beavis and Butthead), also stars Jennifer Aniston (what she was doing in this movie I'll never understand), Stephen Root, Mike Judge and even a cameo by Orlando Jones as a door-to-door magazine salesman.