Quarantine Debates Vol. II: What Is The Best 2000’s Comedy Movie?

Quarantine Debates II, let’s get it.

For this edition of Quarantine Debates, I am going to be choosing the single best comedy movie released between the years of 2000 and 2009. With the way the movie industry has changed this past decade, the 2000’s may go down as the last great decade for traditional, r-rated studio comedy films. The 2010’s certainly had its fair share of successful studio comedies with films such as Bridesmaids, 21 Jump Street & 22 Jump Street, Neighbors, Game Night, Ted, and Girls Trip amongst others, but hits were certainly not as frequent as they had been in past decades. Also, the 2010’s brought a change to the comedy genre in general. Because less and less people started going to theaters in the 2010’s, less studios were willing to spend $40 million on traditional, simple-concept comedy films. So, that led to us receiving our “comedy” films hidden in different and more popular genres. A case can certainly be made that the Deadpool films were the two biggest “comedy” movies of the past decade. Of course, Deadpool looks nothing like what we consider to be the biggest comedy films from the 2000’s, which will be appearing in this debate. In the 2000’s, studios were still frequently spending $20-$40 million on commercially successful comedy movies. Also, the 2000’s brought us a new crop of comedic movie stars and directors. Actors like Seth Rogen, Will Ferrell, Owen and Luke Wilson, Ben Stiller, Jonah Hill, and Steve Carrell really launched, or elevated, their film careers in the 2000’s. And behind the camera, directors like Adam McKay, Todd Phillips, and Judd Apatow dominated the comedy scene throughout the 2000’s. Each of them had their own distinct voice and style, which helped shape the decade as a whole. Ultimately, the 2000’s gave us a great amount of hilarious films, but it is now my job to choose the best of the best.

I decided to settle this debate using a March Madness (RIP, moment of silence) style bracket. I chose 16 films and split them into four regions. The four films in each region were then seeded based on their Rotten Tomatoes score. I will go through each region and decide on a winner in every matchup until there is only one film remaining. The first region is the Ferrell Region. Will Ferrell dominated 2000’s comedies more than any other actor, which earned him a region of his own. The four films in the Ferrell Region, in order of seeding, are: 1. Talladega Nights: The Ballad of Ricky Bobby (RT: 71%), 2. Anchorman: The Legend of Ron Burgundy (RT: 66%), 3. Old School (RT: 60%), and 4. Step Brothers (RT: 55%). The second region is the Apatow Region. Judd Apatow did more for the 2000’s comedy scene, as a director and producer, than anyone else. He made some incredibly memorable films, and helped usher in a new wave of comedy stars. His region is made up of both films he directed and films he produced (note: Apatow did help produce some films in the other regions as well, which just goes too show how much of an impact he had on the genre during this decade). The four films in the Apatow Region are: 1. Knocked Up (RT: 90%), 2. The 40-Year-Old Virgin (RT: 85%), 3. Forgetting Sarah Marshall (RT: 83%), and 4. Pineapple Express (RT: 68%). The next region is the Teen Region. This one is pretty self-explanatory, this region is made up of the best teen comedies of the 2000’s. The four films in the Teen Region are: 1. Juno (RT: 94%), 2. Superbad (RT: 88%), 3. Mean Girls (RT: 84%), and 4. American Pie 2 (RT: 52%). Finally, the last region is the Wildcard Region. Why is it called the Wildcard Region? Well, because this is really just a collection of films I couldn’t find a solid, connecting theme for but needed to be included anyway. The four films in the Wildcard Region are: 1. I Love You, Man (RT: 83%), 2. The Hangover (RT: 78%), 3. Wedding Crashers (RT: 75%), and 4. Dodgeball: A True Underdog Story (RT: 70%).

The Bracket:

(Forgive me for how the bracket looks. I’m a wannabe writer, not a wannabe graphic designer.)

Round One:

The Ferrell Region:

1. Talladega Nights vs 4. Step Brothers

The first matchup I’m going to be breaking down is a battle between two films starring Will Ferrell and John C. Reilly, and directed by Adam McKay. When I was setting up the seeding for this region, I was surprised to learn that Step Brothers was the most poorly reviewed out of these four films, while Talladega Nights was the most positively reviewed. A lot of McKay-Ferrell collaborations, like Step Brothers, seemed to have been initially misunderstood or unpopular with critics, before eventually finding a cult following later on. Based on its Rotten Tomatoes score though, Talladega Nights seems to have been pretty warmly received upon its initial release. Personally, I really enjoy both of these films. Reilly and Ferrell have incredible chemistry in them, which really helped elevate both movies to another level. I do not think either of these films would work as well with different actors in the leading roles.

A common pattern may continue to come up throughout these matchups, which is that the movie I’ve revisited more over the years is the movie that will ultimately advance. I believe what makes a great comedy film is the ability for the jokes to remain funny, even after multiple rewatches. For this particular matchup, Step Brothers remains a film I re-watch, think about, and quote more than Talladega Nights. And oddly enough, despite their seeding, I think that is the common consensus. Perhaps because it has just a few more memorable quotes and scenes, Step Brothers seems to be a bit more present in the current zeitgeist, than Talladega Nights.

Winner: Step Brothers

2. Anchorman vs 3. Old School

Anchorman, another McKay-Ferrell collaboration, was released in 2004 and remains one of the most iconic comedies from the last 20 years. Old School, on the other hand, was released in 2003, directed by Todd Phillips, and played a big role in launching Ferrell’s post-SNL film career. Unlike Step Brothers and Talladega Nights, which largely relied on the team of Reilly and Ferrell, both of these films find their success as a result of their ensemble casts. The list of actors that appear in these two films includes Paul Rudd, Steve Carrell, Vince Vaughn, Luke Wilson, Christina Applegate, Seann William Scott, Jeremy Piven, David Koechner, and of course Will Ferrell. Those were some of the biggest names in comedy throughout the 2000’s.

Unfortunately for Old School, this matchup wasn’t actually that difficult to decide. I love Old School personally, but Anchorman is just in another tier when it comes to great comedies. Anchorman is legitimately just a 90-minute collection of memorable scenes, quotable lines, and hilarious moments. Because of that, it has cemented its place as one of the funniest comedies of all time, in my opinion. It was a must-have when I was thinking of what films to include in this debate, and I was certain it was going to, at the very least, make it past the first round.

Winner: Anchorman

The Apatow Region:

1. Knocked Up vs. 4. Pineapple Express

Kicking off the Apatow region is a matchup between a film he directed, Knocked Up, and a film he produced, Pineapple Express. These films may share Apatow and a few cast members, but truthfully they do not have a ton in common. Knocked Up is perhaps the poster-film for the 2000’s r-rated rom-com genre, while Pineapple Express is a stoner fueled action-comedy. That being said, both films are hilarious in their own right and deserve a spot in this debate.

In many ways, Knocked Up is the definitive Judd Apatow film, so it receiving the number one seed was not a problem for me. Also, it makes sense that the slightly more absurd and high-concept Pineapple Express garnered more of a mixed reaction from critics, making it the number four seed. Unlike some of the McKay-Ferrell films that appeared in the previous region, Apatow’s films have always been driven by their plots. So, I think it is fair to judge these two films based on their respective stories. While the story in Pineapple Express may be more unique, I find the personal, touching, and funny story of Knocked Up to be more appealing. Like many of the films included in this debate, it is by no means a perfect movie. It has its flaws for sure, but Rogen’s performance and Apatow’s script make it one of my favorite comedies from this decade.

Winner: Knocked Up

2. The 40-Year-Old Virgin vs 3. Forgetting Sarah Marshall

Once again, we have a battle between an Apatow-directed film, The 40-Year-Old Virgin, and an Apatow-produced film, Forgetting Sarah Marshall. The 40-Year-Old Virgin was actually Apatow’s directorial debut, and interestingly enough, Forgetting Sarah Marshall was the directorial debut for its director, Nicholas Stoller, who would go on to direct numerous other films such as Get Him to the Greek, The Five-Year Engagement, and Neighbors. These films are definitely more similar than the two films from the last matchup. Like many Apatow films, they are centered on a relationship. They also both took two TV stars, Jason Segel and Steve Carrell, and helped turn them into leading men. But, I would argue their greatest similarity is the wildly funny supporting cast that both films possess. Forgetting Sarah Marshall is full of hilarious actors making small appearances, and The 40-Year-Old Virgin owes as much of its success to Carrell, as it does to Seth Rogen, Paul Rudd, Catherine Keener, and Romany Malco.

Honestly, this is the hardest first-round matchup to judge so far. I absolutely love both of these films, and find them immensely re-watchable. It makes sense that their Rotten Tomatoes scores were so close, 85% for The 40-Year-Old Virgin and 83% for Forgetting Sarah Marshall, because they really are two incredibly enjoyable and hysterical films with a lot in common. At the end of the day though, I have to make a decision. Personally, Forgetting Sarah Marshall is just a little bit more re-watchable for me. I find the supporting performances in that film to legitimately be some of the best of the decade, and the chemistry between Segel and Mila Kunis feels authentic as well. This is a tournament full of the best of the best, which means touch choices have to be made and great films have to be eliminated, which has now happened to The 40-Year-Old Virgin.

Winner: Forgetting Sarah Marshall

The Teen Region:

1. Juno vs 4. American Pie 2

Truthfully, the first matchup in the Teen Region is one in which I don’t feel I need to spend too much time on. American Pie 2 certainly has its moments, and was a film I probably enjoyed a lot more when I was younger, but Juno is the far superior film. In fact, I am going to save a lot of my thoughts on Juno for the next round because this matchup was such an easy one to decide. With all that being said, this is the Teen Region, and no one can deny that American Pie 2 is the sequel to one of the seminal teen films of the past 25 years or so. Also, in a world of shitty comedy sequels, American Pie 2 is actually a pretty decent follow-up in my opinion, which is why it earned a place in this debate initially. But, it was never going to beat the number one seeded Juno here.

Winner: Juno

2. Superbad vs 3. Mean Girls

Now this is a far more difficult matchup to judge than the previous one. The Seth Rogen/Evan Goldberg written, Superbad, going up against the Tina Fey written, Mean Girls, in the first round feels unfair. These films are not just great 2000’s teen movies, they are truly two of the best teen movies of all time. I think it would be fair to say that they both helped form the generation that grew up with them. Furthermore, their iconic characters and lines of dialogue are widely-known, and appreciated, amongst all people under a certain age.

Interestingly, one could make the argument that Superbad is solely a film about male friendships, while Mean Girls is solely a film about female friendship. Their styles of comedy may be slightly differently, but ultimately both of these films have a lot of the same core values and messages, in my opinion. More importantly for this particular debate though, they are both hilarious. Unfortunately for Mean Girls, it will become evident throughout these matchups that, despite its number two seed, Superbad is probably the odds-on favorite to win this entire debate for me. I find it to be funnier than Mean Girls and I have revisited it far more often as well. Mean Girls definitely doesn’t deserve a first-round exit, but sometimes the seeding just isn’t fair.

Winner: Superbad

The Wildcard Region:

1. I Love You, Man vs 4. Dodgeball

First up in the poorly titled Wildcard Region is a matchup between the definitive adult male friendship film, I Love You, Man, and one of the most ridiculously absurd sports films ever made, Dodgeball. These films were released five years apart and stylistically do not have a ton in common. Dodgeball feels more similar to some of the McKay films that came out in the 2000’s, while I Love You, Man has much more in common with Apatow’s films.

Oddly enough, I Love You, Man sort-of feels like the forgotten great comedy of the 2000’s. Perhaps that is because it was a movie centered on male friendship that came out only a few months before The Hangover, which was one of the biggest comedy hits of the whole decade. Regardless, it is one of the most watchable films to come out of this era. Paul Rudd, Jason Segel, and Rashida Jones all give effortlessly funny performances. This is one of those light, quick, easy-to-watch films that you can turn on at any point and immediately get sucked in. Despite its more overtly comedic moments, the film feels incredibly authentic and naturalistic. On the other hand, Dodgeball is a much more preposterously insane experience. I don’t mean that as a critique either. The film’s success is due to its over-the-top and surreal elements. With that being said, Dodgeball strangely feels a little bit more dated than some of the other great comedy films that came out around the same time. Perhaps because movies like The 40-Year-Old Virgin and Anchorman reached a level of iconic status that Dodgeball never quite could, so they remained more relevant, while Dodgeball remained a part of the past. Because of that fact, I Love You, Man, which I believe holds up better than its opponent, wins this matchup.

Winner: I Love You, Man

2. The Hangover vs 3. Wedding Crashers

The final matchup in round one is not as easy to judge as one may think. There is no denying just how massive of a film The Hangover was when it was released, but Wedding Crashers is another wildly successful film that has lived on, and held up, for quite a long time now. The Hangover, released in June of 2009, feels like the last great comedy to be released in this era. It was one of the biggest moments in pop-culture that year, and remained very relevant in the following years because almost every successful comedy to be released during those years was given the title of “the funniest movie since The Hangover.” Like I stated earlier though, Wedding Crashers is a pretty formidable opponent. It remains one of the most memorable and well-liked films to come out during that stretch in the middle of the decade. Also, it contains a great early Bradley Cooper performance five years before the other film in this matchup would help make him a star.

Although Wedding Crashers deserves a lot of the praise I’m giving it, there is just no way a film like The Hangover can be eliminated in the first round. It was too big of an event for it to lose this early on.

Winner: The Hangover

Round One Results:

Round Two:

The Ferrell Region:

4. Step Brothers vs 2. Anchorman

Starting off round two is a matchup between two of Will Ferrell’s most iconic films. In round one I noted that Step Brothers was more re-watchable, and more relevant today, than Talladega Nights. Unfortunately for Step Brothers, it is now going up against the most re-watchable and continuously relevant film of Ferrell’s career, Anchorman. The great chemistry of Reilly and Ferrell in Step Brothers is trumped by the incredible dynamic between Ferrell, Rudd, Carrell, and Koechner in Anchorman. This is a debate of the best comedy films of the 2000’s. Because of that, it is not solely about quality, but about legacy as well. Anchorman is indeed a superior film to Step Brothers in terms of quality, but it also has a far greater legacy. I started this matchup description off by saying these were two of Ferrell’s most iconic films, but the truth is Anchorman is his most iconic film and Ron Burgundy is his most iconic character. It just simply has to win this region.

Winner: Anchorman

The Apatow Region:

1. Knocked Up vs 3. Forgetting Sarah Marshall

The process of deciding which film should advance in the Apatow region is not going to be as simple as the previous region. These two films, released just one year apart, are probably the two best r-rated rom-coms of the 2000’s. It is now up to me though to decide which is number one, and which is number two. Because this is the Apatow region, to make my decision I am going to rely on what is perhaps the most talked-about aspect of his films from a critical standpoint, which is their length. The films Apatow directs are often criticized for being too long. In his attempts to flesh out some of the more dramatic elements of his films, he often loses the viewer’s attention for a bit, or creates sequences that drag on unnecessarily. The official runtime of Knocked Up is 129 minutes, while Forgetting Sarah Marshall‘s is 111 minutes. This may not seem like a huge difference, but I do find that those 18 minutes have an effect on how these films hold up on a rewatch. Both of these films have dramatic elements to them as well as comedic, but the slightly shorter runtime of Forgetting Sarah Marshall makes those elements feel less intrusive. The tone of Forgetting Sarah Marshall is more even and consistent throughout, and I find myself still enjoying every scene when I rewatch it. Although Knocked Up may be the seminal film of Apatow’s directing career, Forgetting Sarah Marshall is the better overall film in my opinion.

Winner: Forgetting Sarah Marshall

The Teen Region:

1. Juno vs 2. Superbad

So, I purposely didn’t spend much time on Juno in round one because I knew I was going to have a lot to say for this matchup. That is because, as great as Mean Girls is, these are probably the two best teen comedies from the 2000’s, and interesting enough they were both released in 2007 (Juno in limited release) and share a star in Michael Cera as well. On the one hand we have Juno, the indie darling penned by Diablo Cody, directed by Jason Reitman, which went on to be a hit at the box office and earn an Academy Award for Best Original Screenplay. On the other hand we have Superbad, which came from a script that childhood friends Seth Rogen and Evan Goldberg started writing as teenagers, and went on to become a commercially successful and generationally important film in its own right. Now, here’s what I’ll say about these two similarly incredible films, while Juno  was a very important film at the time of its release, Superbad feels like the more culturally relevant film in 2020. For some reason, Juno feels more attached to the time it came out, while Superbad feels timeless. I’m sure there are some that may disagree with that, but for me personally, I choose to revisit Superbad far more often than I do Juno. I don’t mean to sound too critical of Juno, it is obviously an incredible film. But, when I think of teen comedies from the 2000’s, my brain immediately goes to Superbad before anything else.

Winner: Superbad

The Wildcard Region:

1. I Love You, Man vs 2. The Hangover

It is now time to decide which film will be joining Anchorman, Forgetting Sarah Marshall, and Superbad in the final four, in a matchup between these two hilarious 2009 comedies. Perhaps the biggest difference between The Hangover and I Love You, Man is that while the former is a pure comedy through and through, the latter is more of a rom-com than anything else. I Love You, Man may be a more endearing story, but at the end of the day The Hangover is just simply a funnier film. It pains me to state that so bluntly, because I do genuinely love I Love You, Man, but I can’t deny how great The Hangover is from a comedic standpoint. When it comes to funniest movies of the 2000’s, I feel like it simply has to be in the top four, which is why it is advancing here. I Love You, Man is great, Paul Rudd is great, Jason Segel is great, Rashida Jones is great … but The Hangover is The Hangover.

Winner: The Hangover

Round 2 Results:

Final Four:

2. Anchorman vs 3. Forgetting Sarah Marshall

Let me start the Final Four off by saying what a run for Forgetting Sarah Marshall. Regardless of whether or not it makes the final, it has established itself as the cinderella story in this tournament. With that being said, it has found itself up against its toughest opponent yet, with Anchorman. When I was judging the matchup between Anchorman and Step Brothers I noted that this debate is about legacy as well as quality. Unfortunately for Forgetting Sarah Marshall, that is going to help out Anchorman in this matchup, just as it did in its last matchup. Forgetting Sarah Marshall is an incredible movie, and clearly based on its success so far I have a lot of admiration for it, but when you think of comedies from the 2000’s, you think of Anchorman. It’s one of the funniest, it’s one of the most quotable, and it’s one of the most memorable. Forgetting Sarah Marshall earned its final four spot. It is one of the very best comedies of the 2000’s, unfortunately Anchorman was a virtual lock for the final.

Winner: Anchorman

2. Superbad vs 2. The Hangover

There is one spot left in the final and it’s going to go to either Superbad or The Hangover. This is an incredibly interesting matchup. I’ve stated numerous times already that The Hangover was a huge hit, and a massive pop-cultural moment back in 2009. But, I’d argue that Superbad is an even more important movie to a generation of film fans. That statement could be seen as controversial seeing as The Hangover more than doubled the box office total of Superbad while in theaters, but I think it is accurate because of how Superbad managed to, and still manages to, resonate with young people. The Hangover is without a doubt one of the funniest movies of the 2000’s, but Superbad has seemingly managed to live on in a way that The Hangover just hasn’t been able to. I’m not saying The Hangover is irrelevant in 2020 by any means, I’m sure somewhere in America there are still some people dressing up Zach Galifianakis’ character for Halloween. But, I can see future generations discovering and loving Superbad in a more substantial way than they might with The Hangover. That idea, mixed with the fact that I just simply enjoy Superbad as a film more than The Hangover, is why Superbad is advancing to the final matchup to take on Anchorman.

Winner: Superbad

Final Four Results:

The Championship:

2. Anchorman vs 2. Superbad

If you were to ask me who the two favorites were at the beginning of this, I would have said Anchorman and Superbad, so I’m not that surprised by this outcome. Both of these films would probably fall somewhere on the list of my top 10 comedies of all time, regardless of decade. I’ve already spent a lot of time discussing what it is that I love about both of these films, so I won’t be discussing their individual merits too much here. Instead, I’ll attempt to look at how they compare to one another, which may be difficult because these are fairly different movies. Superbad is much more of a plot-driven film, while Anchorman is just a connected collection of non-stop jokes and absurdity. I do feel that that distinction is important to consider when deciding on which of these films I prefer. At the end of the day this debate is about what is the best overall comedy MOVIE from this decade. If I’m being honest, I would have to choose Superbad as the better complete movie. Not only is it equally as hilarious and unforgettable as Anchorman, but it comes with a complete story, fully-realized characters, and some genuine heart as well. During Superbad’s first round matchup against Mean Girls I noted that it was realistically the odds-on favorite to win this debate. That is because, even though I am someone who dreads the idea of attempting to make a comprehensive list of my favorite movies of all time, if I were to one day be able to do so, I would have to imagine Superbad finds a spot in the top 20 or 30. I love it that much. It is the best comedy movie of the 2000’s.

Winner: Superbad