Twenty 20-Fav: The Break-Up (2006)

In Twenty 20-Fav, we’re spending 2025 examining the work of actor/director Jon Favreau. This week, we review The Break-Up, an anti-rom-com from director Peyton Reed that finds our boy Favs once again playing second fiddle to Vince Vaughn.

We’ve entered a new era in our exploration of the works of one Jonathan K. Favreau. So far, our boy has established himself as a reliable character actor, a writer/director of canny, personable features, and a solid producer to boot. But now it’s time for his buddies to get in on the action, too.

The Break-Up is the first feature film from Wild West Picture Show Productions, the film division of Vince Vaughn’s production company, Wild West Television. Four of the next six entries in this series will come courtesy of Wild West Picture Show, and next time we’ll even discuss the film that gave the company it’s name.

But for now: The Break-Up.

The Break-Up comes right at the tail-end of the romantic comedy boom that started in the mid-90s and petered out with the rise of the very people involved in this production. “The Frat Pack” is a term coined by USA Today to describe the gaggle of actors and comedians who frequently appeared together in bro-centric comedies about bros being bros. I don’t want to lay the blame on the death of the romantic comedy on folks like Judd Apatow, but then I also don’t think it’s any accident that 2006 was right about the time Apatow and Co. decided rom-coms could be for guys so long as they were two hours long and did all the swears. (This is a whole other phenomenon I truly don’t mean to examine here. Maybe some other time.)

Fortunately, this is probably the closest this entire column will get to having to deal with any Frat Pack movies, because not long after The Break-Up comes out, our boy Favs gets the call from Marvel and from there we’re off to the fuckin’ races.

Favreau’s number one homeboy, Vince Vaughn, is the brains behind The Break-Up, at least as far as I can tell. As mentioned, this comes from Vaughn’s Wild West Picture Show company, and Vaughn gets a ‘story by’ credit. Vaughn is also one of eight listed producers (along with longtime buddy and returning bit player Peter ‘Ralphie’ Billingsley). All told, it’s honestly kinda neat to see all these guys starting to make it in the biz, to the point of actually calling the shots. I admire that. Good for them.

But anyway: The Break-Up.

If you asked me to guess what Vince Vaughn’s contribution to this film’s story was, I’d probably guess, “Hey, I wanna do a movie where I get with Jennifer Aniston!” I mean, who could blame him, right? And apparently that play worked, because the two began dating during production, breaking it off a couple months after the film came out. But then somewhere along the way Vaughn’s plan morphed into a movie where the whole mid-film break-up and resolution endemic to every rom-com became the entire film. It’s not exactly a novel concept, but then it also kinda goes against convention a little bit, which should be no real surprise coming from Down With Love director Peyton Reed. The film they wound up making, though, plays out less like a romantic comedy and more like a dramatic stage play headlined by the biggest goofus on the planet.

The film opens with best buds Gary Grobowski¹ (Vaughn) and Johnny O (Favreau) at a Chicago Cubs game. Johnny is conspicuously the only White Sox fan in the stands, and relishes sticking out like a sore thumb. Gary’s badgering catches the attention of Brooke (Aniston) a few seats down, and the two have a weird little meet-cute over hotdogs. We then get to see snapshots of their budding relationship over the opening credits in the form of a slideshow of cookouts and picnics, camping trips and all sorts of fun times between Gary, Brooke, and their collection of friends.

Only after all this do we get any sense of who Gary and Brooke are as people. Gary runs a Chicago tour bus business with his two brothers, idiot horndog Lupus (Cole Hauser) and idiot finance guy Dennis (Vincent D’Onofrio). Brooke works as a studio curator for a high society abstract artist (Judy Davis). Do any of these details matter? Do they ever? He’s a shlubby forty-year-old fratboy and she’s a budding artist and fan of the finer things in life. One of the first arguments we see them having is over his disdain for ballet and unwillingness to ever take her to one. I’m honestly not sure what either of these people ever saw in each other to begin with, and how diametrically opposed their lifestyles are should be sign number one that none of this will end well. Gary apparently gets by on his ineffable charm and Brooke gets by on her ability to tolerate it, I suppose.

At any rate: The Break-Up.

One night after a disastrous family dinner where Brooke has to prepare everything while Gary plays video games, they blow up at each other and Brooke calls it quits. She goes into the other room, waiting for him to follow her and apologize, but instead Gary quietly grabs his jacket and walks out. He’s not even necessarily calling her bluff, because he’s the kind of guy who takes a woman at her word and assumes “Well I guess that’s that!”

This hurts Brooke, of course, knowing that he didn’t even try to make amends. Instead he goes to complain to his friends, Johnny O and Riggleman (Jason Bateman), while she goes and complains to her girlfriend Addie (The Big Empty‘s Joey Lauren Adams) and Addie’s husband Andrew (Elf‘s Peter Billingsley). But the fun continues, because even though Gary and Brooke broken up, neither is willing to be the one to move out. She stays, hoping he’ll come to his senses; he stays, because he’s a stubborn prick who always gets his way.

I was all prepared to blast this movie for forcing conflict when simply talking about it would solve everything. But they try that. A couple times, in fact. And then comes the conflict. He treats his half of the condo like a bachelor pad; she lets her brother (John Michael Higgins) and his a capella group practice in her bedroom; he replaces the dining table with a pool table; she kicks him off their couples-only bowling team (though her friends still let her stay, which doesn’t seem fair, but Gary is too dumb to make this argument).

Brooke tries everything she can to make Gary mad, or jealous, or just plain sorry, and he never gets the message because he’s a big dumb animal who needs things spelled out for him like a child. At one point Lupus takes him to a club and gives him some truly gross advice for picking up ladies, and suddenly we’ve fallen into Swingers III for a moment (assuming Made is Swingers II), where the shoe is on the other foot and Trent is the one needing life advice. Johnny O even becomes the voice of reason, telling Gary what an entitled prick he is. Will it finally sink in? Will Gary and Brooke finally bury the hatchet? Or will things continue to fall apart?

[PAUSE FOR EFFECT AND MILD SPOILER ALERT FOR A NEARLY TWENTY YEAR OLD MOVIE]

No, of course they don’t patch things up! Because this movie is called The Break-Up! Not The They Get Back Together For No Reason! They told you exactly how this was gonna go in the title, which I realize is not any kind of clever twist or anything, but it’s kind of bold for a mainstream rom-com to end on such a downer note. It’s the hook for the whole movie, but to have them try to reconcile and utterly fail feels… Real. It feels like a more honest depiction of how most break-ups go. This likely came about from the rehearsal phase, where Jennifer Aniston insisted on workshopping the script with Vaughn in an attempt to get more of the woman’s side of the story in there. Good for her, because we really didn’t need another rom-com where the girl exists purely to cramp her man’s style. Brooke has her own agency and her own desires to fulfill.

Brooke tries to reconcile by offering Gary two tickets to see The Old 97’s in concert, a show they were already planning to see before they broke up. He graciously accepts, but when the concert rolls around, Gary is nowhere to be seen. He later admits he got caught up with his friends, but the point is clear: He was never really interested in the first place, and thought she wasn’t really serious about it either. So of course, once she tearily confesses that his complete apathy cut her deep, he goes to talk to Johnny O, who confirms that his complete apathy is how he’s always been. He’s never done anything for anyone else, and considers himself God’s gift to the world for simply being everyone’s bro. Gary takes this to heart and decides to finally take some initiative. He ditches the pool table, sets the dining table and makes a classy dinner for the two of them. But it’s too little too late. The damage has been done and Brooke now has no interest in reconciling anymore. That’s it, they’re done for good now.

It’s a bold move to end on Gary and Brooke agreeing to go their separate ways, even if they eventually do make nice in the film’s epilogue. It’s also not especially funny, which is a criticism I see levied at the film in general from a lot of critics. By this critic’s reckoning, though, it’s right in line with the kind of bro-centric relationship patter Vaughn & Co. delivered in Swingers and Made. If anything, Jennifer Aniston’s influence brings this closer in line with the typical rom-coms of the day. Which, again, is only a good thing. Movies like this need that sort of balance. As it is, though, The Break-Up is less “ha-ha” funny, and more “Yeesh, yeah, that’ll happen” funny. It’s not quite to the level of a cringe comedy, but it’s pretty damn close.

THE FAVREAU DIMENSION

Ol’ Johnny Boy is here to support his buddy Vince. Not even behind the scenes in a producing role, Favreau is on hand purely to play Gary’s voice of reason. Johnny O is kind of a weird character. We first see him clearly enjoying stirring the pot as the only White Sox fan at a Chicago Cubs game. Then later, we see him at work tending bar, dispensing wisdom like it’s his job. Later still, when Gary complains to him that Brooke is out with some other guy, Johnny O very blatantly offers to get rid of the guy, with a sinister gleam in his eye. You don’t know if he’s serious or if he’s just being a goof, but it’s genuinely kind of a creepy moment. It’s that residual wild animal that we used to see glimpses of peeking out again.

FINAL RATING

3.5 stars (out of 5). S’pretty good.

NEXT TIME: It’s the wild west, baby!

1. I have no real way to prove this, but I have a sneaking suspicion someone at RedLetterMedia saw this film in 2006 and stole the name for their 2007 web series The Grabowskis.
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