TALLADEGA NIGHTS: THE BALLAD OF RICKY BOBBY (2006)

Unlike most comedic stars of the decade (collectively known as the Frat Pack), Will Ferrell has continued to headline comedies similar to the films that made him a star. However, his recent efforts haven’t had nearly the same financial or critical success. He’s best known for his work with writer-director Adam McKay, and their partnership includes Anchorman: The Legend of Ron Burgundy, Talladega Nights: The Ballad of Ricky Bobby, and Step Brothers. Now, there’s no denying the legacy of Ron Burgundy, but when I think of Ferrell’s man-child schtick mixed with McKay’s absurdist sensibilities, Talladega Nights: The Ballad of Ricky Bobby is the one I consider the best of their collaborations. Aside from the hilarious and quotable lines (“Shake and Bake!”), the film exemplifies absurdism comedy at its finest. It feels as if, in the universe of Talladega Nights, anything goes. One can birth a child by braking at 200 mph, a child can expertly steer a car through oncoming traffic, and a racecar driver can just leave in the middle of a race to eat a sandwich. Everything I just said happens within the first 10 minutes of the movie. Combine that absurdity with layered commentary on American exceptionalism and some impressive racing sequences, and you’ve got a memorable, laugh-out-loud comedy that takes you for one helluva ride!

TROPIC THUNDER (2008)

You’d be hard-pressed to find a more iconic action comedy from the 2000s than Tropic Thunder. Prominent Frat Pack member Ben Stiller directed, co-wrote, and led an all-star ensemble, including Jack Black, Jay Baruchel, Matthew McConaughey, Tom Cruise, and an Academy-Award-nominated Robert Downey, Jr., in this satirical movie about the lengths actors will go to for a good performance. Controversial, yet timeless, Tropic Thunder’s memorable characters, extreme plot lines, and hysterical parody trailers that start the movie all contribute to a brilliant lampooning of the movie industry and the egotistical stars that populate it. Tropic Thunder has insane performances and meta-commentary locked and loaded for anyone trying to get some. 

BORAT: CULTURAL LEARNINGS OF AMERICA FOR MAKE BENEFIT GLORIOUS NATION OF KAZAKHSTAN (2006)

Borat is simply a comedy sensation. Sacha Baron Cohen’s ingenious mockumentary sees him don the iconic moustache and suit to travel across America to interview unsuspecting citizens. Some of its humour can be viewed as offensive, but similar to Tropic Thunder, it’s all in service of a commentary on the casual ugliness of American culture, a culture that’s seemingly gotten worse according to its sequel, Borat Subsequent Moviefilm. Borat is the definition of a comedy classic, and I’m willing to bet top-dollar that you’ve uttered the phrase “Great success” or “My wife” in Borat’s iconic accent at least once. It’s an Academy-Award-nominated, box-office phenomenon that will be studied and examined for a long time. Very nice, indeed.

SUPERBAD (2007)

On the surface, Superbad may seem like another typical coming-of-age high school sex comedy. Two teenagers trying to lose their virginities before college is not something I would call unique. Yet, Superbad is an undeniable classic that has turned into maybe the quintessential high school comedy, launching the careers of Jonah Hill and Michael Cera in the process. What makes this film such a classic, beyond how funny and wild it is, is its relatability. Sure, certain extremes, like McLovin’s (Christopher Mintz-Plasse) “hanging with the the cops’” storyline, are just hysterical, but its heart is what makes this film work. The friendship between Hill’s Seth and Cera’s Evan in the face of complicated uncertainties makes for a quietly poignant story. 

KNOCKED UP (2007)

I wouldn’t be able to forgive myself if I didn’t mention writer-director Judd Apatow at least once. Between The 40-Year-Old Virgin and Funny People, Apatow has carved a niche for relatable and mature rom-coms, and nowhere is that better illustrated than with Knocked Up. The one-night-stand-turned-lovers relationship between career-ambitious Allison Scott (Katherine Heigl) and slacker stoner Ben Stone (Seth Rogen) plays as real as you can imagine, giving this one some true depth. And while the heart is very much there, it’s a hilariously raunchy movie. Rogen’s interactions with his friends are a definite highlight, but so is the relationship between Paul Rudd and Leslie Mann, which launched a spinoff movie, This Is 40. Bawdy and insightful at the same time, Knocked Up launched Rogen into stardom, and was both a critical and box-office hit. It continues to impress and guide filmmakers for what a rom-com can be.  

WEDDING CRASHERS (2005)

While we’re on the subject of rom-coms, Wedding Crashers is a bizarrely simplistic one, yet it’s endlessly quotable and funny at the same time. Yes, it follows the “scumbag guys learn to love” plotline to a tee, and it begins and ends about as you expect, but it’s what happens in the middle that gives the film an identity of its own. Frat Pack members Owen Wilson and Vince Vaughn give this film a lot of crackling energy just by being themselves. The banter between them gives the movie much needed life, thanks to their rapid-fire dialogue and high joke-per-minute rate (with most jokes being improvised, I imagine). The chemistry between the two stars and the genuine feeling of romance that you can feel through the screen make Wedding Crashers a must-see rom-com for all fans. Bradley Cooper's borderline psychotic performance deserves an honourable mention as well. 

WALK HARD: THE DEWEY COX STORY (2007)

Long before Bohemian Rhapsody and Elvis, we had Walk Hard: The Dewey Cox Story, a pitch-perfect parody of the musical biopic that expertly picks apart the tropes and cliches to hilarious results. John C. Reilly’s performance alone, which is silly yet purposefully melodramatic, makes this a memorable watch that sees the fictitious musician’s comically fast rise (his first song only takes 30 seconds to become a hit) and downfall done in flawless parody fashion. From the start, the movie is hilariously over the top, with one of the funniest and most shocking deaths I can remember. The songs are surprisingly catchy, and the entire cast is committed to the bit too. Walk Hard should be considered a classic, but it remains a true underrated gem. If you haven’t seen it yet, you definitely want a part of this shit.

SHAUN OF THE DEAD (2004)

I’d love to put both of Edgar Wright’s comedy classics from the 2000s in here, but I didn’t want my bias for one of my favourite directors to show. Even still, Shaun of the Dead is a masterclass of horror comedy and hyper-stylized humour. Wright’s sensibilities for frenetic editing and witty comedy make his take on the zombie genre a truly one-of-a-kind experience. Hyper gore, needle drops, and visual gags galore, Shaun of the Dead is a terrific part one to what would turn out to be the Three Flavours Cornetto Trilogy, also consisting of Hot Fuzz and The World’s End. Even if you’re not a big horror fan, Shaun of the Dead is an endlessly endearing film for anyone to enjoy. 

SCHOOL OF ROCK (2003)

I would be remiss if I didn’t mention at least one Jack Black star vehicle, and if I’m being honest, School of Rock was an easy choice. Even when a film isn’t great (or even good for that matter), Jack Black’s complete commitment to character elevates the film. So, imagine what happens when the material is already great to begin with, as it is with this film. Black’s too-cool-for-school insanity makes for a surprisingly lovely film featuring a fun and colourful cast of child actors giving endearing performances that almost match Black’s… Jack Black-ness. But beyond Black, School of Rock is endlessly hilarious and weirdly inspiring in its own weird way. You’ll surely want to rock on after watching this. 

MEAN GIRLS (2004)

I’m just gonna say it: Mean Girls is not fetch. Or maybe it is. I’m still not totally sure what it means. Either way, beyond Mean Girls’ quotability and overall message, it has remained a comedy staple for nearly two decades due to the comedic sensibilities of Tina Fey, which, when mixed with the themes of the film, creates something that makes it hard to hold in laughter. The ensemble is hysterical, featuring an inspired comedic turn from Lindsay Lohan and iconic performances from Rachel McAdams, Amanda Seyfried, and Lacey Chabert. For the time it came out, the film’s refreshingly female-focused high school story made for a fresh take on the genre, and its impact has only elevated over time through meme culture and analysis. Pretty grool, if you ask me.