In Twenty 20-Fav, we’re spending 2025 examining the work of actor/director Jon Favreau. This week we hit the road with Vince Vaughn’s Wild West Comedy Show, a documentary about a ragtag group of stand-up comics on a month-long comedy death march across America.
In the mid-aughts, multi-comedian showcases were all the rage. You had The Original Kings of Comedy, The Blue Collar Comedy Tour, The Comedians of Comedy, and a whole host of others that now litter the DVD shelves at your local Goodwill. All these documentaries showcased the comedians and their acts, giving us a backstage look at how these folks interacted offstage, and let those of us who couldn’t see them live enjoy it from the comfort of our homes. And right in the middle of it all was The Wild West Comedy Show1.
The film’s full title is Vince Vaughn’s Wild West Comedy Show: 30 Days & 30 Nights – Hollywood to the Heartland. Ain’t no way I’m writing that out every time, so from here on in we’re cutting that shit down to just Wild West Comedy Show. Anyway, let’s get into it…
In the summer of 20052, Vince Vaughn had hit peak popularity. Wedding Crashers was the comedy of the summer, becoming the fifth highest-grossing movie of the year behind a Star War, a Harry Potter, a Spielberg, and a Narnia. So after production wrapped on The Break-Up, Vaughn wanted to use his star power to give some of his comedy buddies a boost. He loved the idea of Buffalo Bill’s frontier-themed variety shows of the 1880s, so he created one in his own image for modern audiences.
Vaughn recruited longtime buddies Peter Billingsley and Jon Favreau to help set up the tour, then rounded up four stand-up comedians and hit the road for thirty shows in thirty cities across thirty nights. The idea was that he wanted to bring comedy to cities that don’t typically see big stand-up tours. But while we do make several stops in some of the smaller cities across the midwest, we also spend a lot of time visiting all the usual suspects. Hell, the tour starts in Los Angeles and spends most of the first week bouncing around southern California before finally crossing state lines for Las Vegas. Only when we get to Vegas do they pull back the curtain a bit and you realize the scope of this tour. These guys aren’t playing the Colosseum at Caesar’s Palace, they’re playing the back room at the Golden Nugget. You get the impression that this tour was thrown together pretty quickly. They booked whatever venues would have them, then spun it after the fact as a more intimate show “for the fans”.
The comedians featured in this doc are all pretty typical of the mid-aughts comedy scene. They’re all Dane Cook wannabes to one degree or another. John Caparulo comes out in a plain white t-shirt and ball cap looking and acting like Larry the Cable Guy’s angry little brother. Bret Ernst identifies himself with some quick “Look at me, I’m a guido” shtick, which is honestly pretty funny because it then immediately cuts to Sebastian Maniscalco acting like he just fell out of The Sopranos. And then rounding out the lineup is Ahmed Ahmed, who brings some much-needed perspective to this crew, as his sets are almost exclusively about being an Arab in post-9/11 America. (This was 2005, after all.)
Every one of these guys’ acts is like a signpost for the era in one way or another. Maniscalco, especially, feels like the kind of comedian that got left in the dust sometime around 2010. (The guy’s starring in movies now, so I guess he did something right.) All his jokes are about how men should be ashamed to wear flip-flops or drink flavored coffees, while at the same time bragging about how overly-manscaped and chiseled he is. This guy… This is not my kinda guy. But he fits right in with Vaughn’s crew, and you can see it in the audiences that turn up for these shows. They love these guys. The seats are packed with college girls and bros who just ate this shit up with a spoon.
This, incidentally, was during my sophomore year of college. I was aware of this tour taking place because I’d been dragged to see Wedding Crashers with a bunch of dorm-mates (wasn’t a fan), so it was kind of hard not to be aware of whatever Vince Vaughn was doing at the time. I was not the target audience for this, plain and simple.
But looking at it with some distance, it makes for an interesting time capsule. Ahmed Ahmed’s bits hit particularly hard, as he tells stories of getting detained at airports and police stations just for the crime of being born in Egypt and not looking white. He talks about doing a dozen stops on this tour where he realizes he’s the only Muslim in the room. Things get real and you can tell the tour had a genuine effect on him. And then Sebastian Maniscalco does a joke about putting Axe body spray on his weiner. This comedy thing’s a balancing act; you gotta let the clowns do their thing if you wanna bring down the mood every once in a while.
That tonal clash manifests in the tour itself, as the film is forced to confront the aftermath of Hurricane Katrina. The storm had just hit the gulf coast like a freight train a month prior. Our guys arrive in Texas just in time for another hurricane to hit, delaying the tour. It’s been forgotten in the aftermath of Katrina, but a second category-five storm, Rita, came in just a month later and wreaked even more havoc on the gulf states. The tour stops in Birmingham, Alabama where Peter Billingsley has to inform the four comics that they’re gonna be shipped out to a refugee center to hand out free tickets for that night’s show. We’re told the proceeds from the next few shows will be going to disaster relief, which is great, but you sure wouldn’t know it by looking at anyone’s faces.
By the end of the documentary, I was kind of hoping something dramatic might happen, and it simply never does. On the first night of the tour, director Taylor Hackford is on hand (in the audience, not behind the camera), and tells us that he’s curious to see how different this tour looks after three weeks on the road. You’d hope these guys would melt down or come to blows over something stupid, but it just never happens. Everyone is visibly tired by the time the tour ends in Chicago3, but the whole thing was set up so that we’d end on a homecoming for Vince Vaughn. So instead of a glorious flameout, everyone just puts on their happy face and finishes the tour, the end.
Before this, though, we make a pit stop in South Bend, Indiana, where the guys visit Notre Dame. Vaughn says it’s the first time he had been back there since filming Rudy, and wonders how different his life might have been if he hadn’t taken that role and met Favreau on the set. It’s the little glimpses of the real Vince Vaughn that pop up here and there that start to make this doc kind of worth it. You can tell he values the friendships he’s made throughout his career. Dodgeball co-star Justin Long and Wedding Crashers co-star Keir O’Donnell pop up frequently on the tour, and Vaughn can’t resist the chance to bring them both onstage to play some improv games with the audience. Even Peter Billingsley gets some time to shine, as Vaughn relishes the chance to show a clip of the after-school special where the two first met4.
Keir O’Donnell even joins the comics as they visit some of the families displaced by Hurricane Katrina. As they introduce themselves, one kid immediately lights up when he recognizes O’Donnell from Wedding Crashers. “You’re the gay dude!?” he says, laughing hysterically. It’s a little awkward in retrospect, but then we see that family backstage at that night’s show, and everyone seems really happy to be there.
Wild West Comedy Show is ultimately a vanity project for Vince Vaughn more than it is a showcase of up-and-coming comedians. Two of these guys would go on to star in movies and TV shows of their own (and one of them will appear in this series again very soon), so the showcase must have given them some kind of boost. The doc really doesn’t do anyone’s set any kind of justice, though. You get a little taste of each comic’s style, but the film is more concerned with the production as a whole. Can these guys make it on the road for a whole month without killing each other or themselves?
The simple answer is: Yep, they sure did.
THE FAVREAU DIMENSION
Jon Favreau shows up for the first night of the tour and, because I guess they still really didn’t know what the show was even going to be, he joins Justin Long onstage and they do the casino scene from Swingers. Justin Long plays Trent, and Long’s Vince Vaughn impression is pretty hilarious, made even better thanks to quick cuts back to Vaughn, who looks genuinely embarrassed. Favs really doesn’t show up for much more in this, but I think it’s cool how often Vince Vaughn keeps talking about him throughout. He knows good and well who helped get him to where he is.
FINAL RATING
2 1/2 stars (out of 5). S’okay.
NEXT TIME: We’re taking a little detour.
- For what it’s worth, this movie is not streaming online anywhere. I found a used DVD copy on Amazon for $2.50.
↩︎ - Filmed in the summer of 2005, the doc premiered at the Toronto International Film Festival in 2006, but wasn’t released theatrically until February of 2008.
↩︎ - Chicago, a city no comedian has ever visited.
↩︎ - It’s the first episode of CBS Schoolbreak Special’s eighth season, titled “The Fourth Man”. If you really want to, you can watch the whole special on YouTube. ↩︎
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