- Jim Carrey, The Cable Guy, 1995. After Chris Farley had to pass, Stiller (better suited to the Matthew Broderick role) decided to star as well as direct. After a week, Ben realised (like Peter Sellers among others before him) that this was not as easy as Chaplin made it look. For a then record $20m, Carrey took over. Well, he would, wouldn’t he.
- Billy Bob Thornton, A Simple Plan, 1998. In the mid-90s, as directors like Mike Nichols and John Boorman hemmed and hawed, Stiller decided to helm and co-star with Brad Pitt as guys finding stolen loot and trying to get rid of it.
- John Turturro, Monkeybone, 2001. Had to quit voicing the titular role due to complications with Mystery Men. "There's an old saying in Hollywood: It's not the length of your film, it's how you use it."
- Sam Rockwell, Confessions Of A Dangerous Mind, 2002. The studio was not sure if new director George Clooney's choice (from Galaxy Quest, Charlie's Angels, The Green Mile) could carry a movie. His test, however, was the best.
- Adam Goldberg, The Hebrew Hammer, 2003. Goldberg said he has to make director Jonathan Kesselman's movie when he read the line: "Shabbat shalom, motherfuckers!"
- Paul Rudd, Anchorman: The Legend of Ron Burgundy, 2004. Stiller was named in Will Ferrell and Adam McKay's script that also called for Dan Aykroyd, Alec Baldwin, Ed Harris... and made an uncredited cameo appearance.
- Johnny Depp, Charlie And The Chocolate Factory, 2004. He was actually considered even after being the record winner of the most Worst Actor Razzie nominations in one year: Along Came Polly, Anchorman: The True Legend of Ron Burgundy, Dodgeball: A True Underdog Story, Envy and Starsky & Hutch. His sixth 2004 film missed the cut: Meet The Fockers.
- Michael C Hall, Dexter, TV, 2006-10. Everyone from John Cusack to Jake Gyllenhaaal - and quite stupidly, Tom Cruise, Sean Penn and Ben! - were listed for TV’s most unlikely hero. Dexter Morgan was the Miami PD’s blood-splatter expert moonlighting as a serial killer... of other killers.
- Will Ferrell, Blades of Glory, 2007. Yeah, sure! But, er, hang on, no! Chazz Michael is pretty much like all my other chaaacters... Oh, they were all sex-addicted, improvisational, world figure ice-skating champs, as well?
- Simon Baker, Sex and Death 101, 2007. “I ended up writing the movie that I wanted to see,” said director Daniel Waters (Heathers, 1988), who scripted it on and off for some 15 years. “Ben loved the script and he was thinking of doing it for awhile. I’ve always said that if Ben had done the film, it would have been the Richard Benjamin movie. With Simon, it ended up kind of being the Warren Beatty movie.”
- Matthew McConaughey, Tropic Thunder, 2007. The idea was born 20 years earlier when auteur Stiller heard his pals in Hamburger Hill and Platoon actually believing their boot camp trainbg made themreal soldiers!! Stiller was first going to play Rick Peck with Keanu Reeves in Stiler’s final role of Tugg Speedman - modeled on Sly Stallone The Younger.
- Will Ferrell, Megamind, 2009. Stiller and Robert Downey Jr were approached for Megamind, a kinda Lex Luthor, versus a kinda Superman (Brad Pitt as Metroman). They were busy. Unfortunately, Ferrell was not.
- Jim Carrey, Mr Popper's Penguins, 2009. Like Jack Black and Owen Wilson, Stiller (and his Greenberg helmer Noah Baumbach) took a great interest in the update of the 1938 book by Sean Anders and John Morris. There, Popper received a penguin in the mail. Here, Carrey’s tycoon inherits them and, said Fox, “comes to understand the importance of family - human and otherwise.”