In The Dilemma, Vince Vaughn plays a man who witnesses his best friend's wife cheating with another man. Ron Howard's latest film is a departure of sorts for Vaughn compared to other films if only because the overall tone cannot be described as a "laugh riot." Still, how did Vaughn become one of the most bankable comedy stars in Hollywood after beginning his career in drama? You can always trace a direct line through a handful of important roles to illustrate what led to an actor's current success, and with Vaughn, that line was definitely on a downward slant until Todd Phillips came along and cast him in Old School. Let's look at eight performances -- including one of his earliest -- that trace the evolution of one Vincent Anthony Vaughn.
21 Jump Street (1989)
Other than an appearance as a motor pool driver in China Beach, this was Vaughn's first role. Johnny Depp and Peter DeLuise (part of me is still sad that we don't live in a world where Depp and DeLuise became the new Burt Reynolds and Dom DeLuise) investigate the murder of a high school teacher's wife and, along the way, we meet a pretty unrecognizable, fairly straight laced Vaughn trying to convince another student to let them into the ice skating rink after hours. This guy! Already up to hijinks! Considering that the character Vaughn is speaking with is named Mike, it's hard not to see a little foreshadowing to the movie that would make him a star seven years later.
Rudy (1993)
Rudy is to Vince Vaughn and Jon Favreau what School Ties is to Matt Damon and Ben Affleck. Rudy, not Swingers, was technically Vaughn's first collaboration with Jon Favreau, a collaboration that would span five more films. In the seminal sports film, Vaughn plays the character of Prick VonAsshole* who doesn't very much like our hero, Rudy Ruettiger -- a walk-on trying to make the Notre Dame football team. When Vaughn says, "He's just a showboat, man," we get our first glimpse of the Vaughn to come in future years.
*Prick VonAsshole is not his character's real name.
Swingers (1996)
Pretty much every line spoken by Trent in Swingers has been co-opted by every 22-year-old male visiting Vegas for the first time over the last 15 years (15 years, really?). If you haven't watched it in awhile, it is a bit shocking to see this Vince Vaughn again -- the hyper-slim, hyper-talking hip version versus the more schlubby version that we all know and love today. Regardless, because of this film, Vaughn went from tiny roles in direct-to-video films to something called...
The Lost World: Jurassic Park (1997)
When looking at Vaughn's filmography, this is the one that's probably the most peculiar. After the buzz of Swingers, there was no question that Vaughn was going to become a star... but the star of what? This is Exhibit A for any situation where Hollywood executives know they have a future leading man on their hands, but don't quite know what to do with him. "Cast him in the new Jurassic Park movie, we will figure it out after that!" Well, after The Lost World, action movies were not in Vaughn's future (unless you count the comedic relief he provided in Mr. and Mrs. Smith), but neither were comedies, at least for some time. Vaughn was to become a dramatic leading man whether the public wanted it or not.
Return to Paradise (1998)
My God, this movie is depressing. For those who have forgotten, Vince Vaughn used to make films with plots that involved the threats of execution from a Malaysian drug bust. In Paradise, Vaughn must make the decision to return to Malaysia to face jail time in order to save the life of his friend (Joaquin Phoenix), who was arrested and faces execution. Not exactly Dodgeball. For five years, Vaughn would go on to make drama after drama including the now infamous scene-by-scene remake of Psycho.
Domestic Disturbance (2001)
The movie that ended Vince Vaughn's career -- at least the dramatic one. Vaughn stars opposite John Travolta (this, perhaps, should have been a red flag) as an evil stepfather (another red flag!) in the long-forgotten thriller. This was also the infamous film that had Vaughn involved in a bar fight with a local North Carolina man. If that local North Carolina man was yelling, "Why won't you do comedy? You'd be so much better at comedy!" as he traded blows with Vaughn, we all owe this man our gratitude.
Wedding Crashers (2005)
I got dumped right before I saw Wedding Crashers for the first time. I saw it three more times at the theater, not because it was just that good, but because Vince Vaughn was just so much fun to be around. The guy always looked like he was having the time of his life in this film. Expanding on the comedic work that he had already done in Old School and Dodgeball, he put everything together for this box office smash. The story of two pick-up artists who, of course, crash weddings grossed $285 million worldwide. Vaughn would re-team with director David Dobkin a few years later for the not-anywhere-near-as-good-successful Fred Claus.
The Break-Up (2006)
The problem with being one of the "It" comedy stars is that you are offered a lot of money to do a lot of crap, and Vaughn is no exception -- Couples Retreat, Four Christmases, and Fred Claus would all qualify. On the other hand, The Break-Up is a good example how Vaughn's dramatic side can enhance his comedic roles, bringing them more depth. Sure, The Break-Up has funny moments, but that's not what drives the film. For anyone who has ever had to co-habitate with an ex, The Break-Up doesn't shy away from the realities of the situation. This is almost a drama with some funny moments, and a lesser actor wouldn't have been able to convincingly pull that off. Though, not really the same type of film, the tone of The Break-Up is a similar one to what you will find with Vaughn in his new release, The Dilemma.