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Written by: Chase Gifford

After searching through more pages of IMDb than I care to admit, along with multiple other sites, I have come up with my own personal Top Ten R Rated Comedies of the Last Decade (2004-2014, so far). If you disagree, great! Let’s discuss it in the comments below.

The films in my list all meet certain criteria that I set in order to form the list. Certain characteristics that came into account are relatability, originality, brazenness, creativeness, quotability, and longevity. Not every film hits absolutely every specific aspect, but all of these hit a number of them. These are films that have stuck with me from the moment I saw them in theaters and continue to do so to this day.

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10. Clerks II (2006)

I will admit, I’m a bit of a Kevin Smith fanboy, sue me. I love the original Clerks, but I hadn’t been introduced to the original until the sequel hit theaters. It’s a simple but poignant story about growing up, even if you’re already middle aged. Being in a similar state of not knowing what I truly want in life, this story is more affecting than ever before. Not to mention it is just plain funny throughout. [Clerks 3](movie:388513) can’t get here soon enough.

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9. Goon (2011)

This is the most underrated and unheard of on the list. HocGoonkey movies have been done in the past but of course not all of them are worth the effort they require to sit through. Goon is one of the exceptional few that outshine the rest of the mediocre sports films. Not only is it funny, it’s very violent and showcases the brutality of hockey; you might even say it embellishes the fighting a bit but it’s all for entertainment. It’s filthy, but has a heart underneath all the curse words and talk of gang bangs. Above all, it is memorable with likable characters and ends with a sequel not only possible but actually happening. Written by Jay Baruchel and Evan Goldberg, this is Apatow comedy without all of the usual actors; aside from Baruchel of course. This was a very pleasant surprise going in completely cold.

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8. Three Flavors Cornetto Trilogy (Shaun of the Dead, Hot Fuzz, The World’s End)

(2004, 2007, 2013)

I am cheating on this one and placing three films in one spot. The unofficial ‘Three Flavors Cornetto Trilogy’ recently finished last year with what I consider to be the best of the three. It all started with Shaun of the Dead in 2004, which quickly gathered a cult following garnering its two “sequels”- 2007’s Hot Fuzz and 2013’s The World’s End. All three have the same or similar ingredients that add up to make three excellent comedies. To name a few; Edgar Wright wrote and directed all three films which star the comedic geniuses Simon Pegg (who co-wrote with Wright), and Pegg’s partner in crime, Nick Frost. All three take familiar genre topics and make them wholly original and unique. All are rampant with quick wit, fast but funny editing, and characters that are truly laughable in the greatest ways possible.

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7. 50/50 (2011)

This is arguably the most serious film of the bunch. Based on the director’s real life experience of dealing with cancer, 50/50 is honest and approaches a touchy subject the best way possible, with a sense of humor. We all have people in our lives that would truly shatter our world if we were to ever lose them. This is about one man dealing not only with a life threatening illness but with those who can’t quite grasp the full spectrum of his situation, himself included. It’s about denial and hopefully, eventually, acceptance no matter the severity of the situation. And believe it or not, it showcases this all with wit and tenderness. It’s funny but touching, and that’s something special.

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6. Forgetting Sarah Marshall (2008)

This is the first time I was really introduced to the comedic prowess of Jason Segel. He did appear first in Knocked Up, but this film is where he not only wrote but also starred alongside a comedy powerhouse of people to back him up. With people like Bill Hader, Jack McBrayer, Paul Rudd, and of course Jonah Hill, this couldn’t fail if it wanted to. The subject here is unhealthy obsession of one’s ex. It isn’t normal behavior but if it’s portrayed right as it is here, it can be a highly entertaining and always quotable comedy classic. Some say this was the film that unfortunately started Russell Brand’s career, but as someone who doesn’t mind Brand, I say so what?

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5. Pineapple Express (2008)

When Superbad was released on DVD, an extra on the special features was a five minute exclusive look at a comedy called Pineapple Express. With a funny window into what this movie could be, the anticipation grew. When it was finally released it became one of the most quotable comedies in decades. With funny moment after funny moment carried by lovable characters, this is one the funniest films to come along in a while. This is one of many Apatow created films that truly hit the sweet spot of comedy, becoming something more than memorable; it’s a modern classic.

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4. The 40-Year-Old Virgin (2005)

This was the start of the Apatow madness that continues even today. Not only did this film jettison Apatow’s career it also made Steve Carell a household name. With Carell’s strong personality, and an intelligent script co-written by Carell himself, this is arguably a comedy must-have in any movie collection. It’s filthy but honest when it comes to the topic of losing one’s virginity, and the false importance given to losing it sooner rather than later. This also has a wonderful supporting cast that includes Catherine Keener, Paul Rudd, Seth Rogen, Jonah Hill (briefly), Elizabeth Banks, Leslie Mann (Apatow’s wife), and the always amusing Jane Lynch. This was the beginning of a lot of careers and its legend is still as strong as ever.

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3. Knocked Up (2007)

Knocked Up was the original grouping of the Apatow comedy dream team that came before This Is the End. This movie is essentially the “team” riffing off of one another with a script thrown in to give it some solidarity. Not only does it speak on the necessity of safe sex, it shows that the most unexpected and maybe even unwanted aspects of life can be the greatest things in our lives. Friendships are in the balance, new relationships are on rocky waters, and it all plays out naturally and hysterically. The best part, in my opinion, is that it shows that a comedy with a heart and a mind is equally as funny as any mindless comedy. It has substance with a smile and it’s a joy to experience.

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2. The Wolf of Wall Street (2013)

I mentioned in one of the first paragraphs that brazenness was something I needed in a comedy and this movie is the very definition of brazen. This is the most fearless film on the list and it’s such a dark story you almost feel guilty for laughing. It makes you wonder if you’re like these very deplorable characters that are, amazingly, based on actual people. That’s a Marin Scorsese film; funny but horrifying. This was my favorite film of 2013 and is one of my all-time favorite comedies. It contains an Oscar worthy performance from the Über talented Leonardo DiCaprio and the twice nominated, Jonah Hill. These characters are horrible, but in a way they open a window that most don’t want to look through and it’s fascinating to watch.

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1. Superbad (2007)

This is hands down my favorite comedy of all-time. For me personally, Superbad is relatable, hilarious, brazen, lasting, and it’s the most quotable film amongst myself and my friends. Specifically speaking about myself and my best friend, Phil, the characters of Seth and Evan are so much like us it’s scary. There is a certain scene near the end of the film that involves the two characters waking up in sleeping bags; it’s the initial words that they mutter that really caught my attention. I have had the very same “conversation” with Phil that basically just consisted of me cursing and him greeting the day. This is just the surface of the similarities to my life and it’s hysterically entertaining. I first saw this on its opening weekend and from that day on I haven’t stopped quoting it. It’s difficult to fully explain why this is my favorite; all I know is it hits me in a certain way that makes me cry with laughter and connects me to characters I maybe shouldn’t be so upfront about being so similar to. It also just happened to release the year I graduated high school. This is the quintessential high school comedy for the current generation and will remain atop my list for a long time to come.

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