It never gets old to rewatch the funniest R-rated comedy movies of all time, as they’re crowd-pleasers and often surprisingly heartfelt films. However, when a movie gets an R-rating, it’s often because there are raunchy or risqué elements within the story, which don’t always age well when viewed through a modern lens. Fortunately, these projects have overwhelmingly stood the test of time, avoiding common pitfalls that can date a movie and disrupt the audience’s enjoyment.

While there are plenty of weird comedy movies from the 2000s, there are also some all-time great films that have become classics of the genre. The early 2000s were an amazing decade for comedy films. Some of the best R-rated projects from the past ten years were clearly inspired by the great movies of the past. Whether they follow a familiar formula or are ground-breaking in style and structure, there’s a lot to love about these works, and it’s exciting to show them to new audiences, experiencing them for the first time.

8

I Love You, Man (2009)

Directed by John Hamburg

I Love You, Man is a love story about one of the most important and most forgotten relationships in cinema: friendship. A heartfelt exploration of loneliness and how hard it can be to make new friends as an adult, I Love You, Man sees Paul Rudd and Jason Segel form an unlikely but true friendship that changes both their lives. It’s a touching reminder of how important it is to connect with friends and build a life outside of a romantic relationship.

Though it’s anchored by its deeper themes and poignant message, I Love You, Man is still a comedy through and through. It puts Peter (Rudd) and Sydney (Segel) in unexpected and difficult situations at every turn. Though Rashida Jones plays the role of the straight man as Peter’s fiancée, Zooey, she still gets to have a lot of fun throughout the story and helps round out the male-driven story. The healthy and genuine friendship at the heart of I Love You, Man makes it easy to appreciate the film, no matter how many times you rewatch it.

7

Palm Springs (2020)

Directed by Max Barbakow

One of the coolest time loop movies to come out in recent years, the delightfully charming Palm Springs pays tribute to the best parts of the genre while simultaneously distinguishing itself. It would be easy to immediately compare Palm Springs to Groundhog Day, as both are rom-coms with a sci-fi twist, but Palm Springs pulls both its protagonists into the loop, developing their relationship from there. Andy Samberg and Cristin Milioti are pitch-perfect as Nyles and Sarah.

Their chemistry flows and feels natural from the minute they share the screen, instantly making the audience care about what happens to the couple.

Their chemistry flows and feels natural from the minute they share the screen, instantly making the audience care about what happens to the couple. Set in the idyllic Palm Springs against the backdrop of a wedding, the movie makes good use of these elements, juxtaposing them with the nihilism the characters feel while they’re stuck in the loop. However, by the end of Palm Springs, both the audience and characters have regained their purpose and desire to live life to the fullest.

6

Animal House (1978)

Directed by John Landis

Of all National Lampoon’s film projects, Animal House might be the best-known and most enduring. Tackling the raunch and hilarity of university fraternities, Animal House features a star-studded cast with John Belushi playing one of his most iconic roles, Bluto. Though packed with chaos and sometimes nonsensical, Animal House appeals to the parts of its audience that can relate to the antics of young adulthood and the intensity of the college parties of old.

For an R-rated comedy from the late 1970s, Animal House has aged surprisingly well. There are dated elements that can’t be ignored, but these are far less distracting than similar projects of the era. Most importantly, Animal House isn’t afraid to poke fun at itself and acknowledges how silly and offbeat some of the comedy is, which successfully lets the audience in on the jokes. The film is a non-stop ride of adventure and action, taking the viewer on an unforgettable and hilarious journey.

5

Knocked Up (2007)

Directed by Judd Apatow

It would’ve been easy for Knocked Up to rely on cheap jokes and simply put its characters through the wringer, but Judd Apatow’s hit comedy does a lot more than that. Katherine Heigl and Seth Rogen are at their best in Knocked Up, a rom-com that upends the traditional structure of relationships. Instead of falling in love and eventually deciding to have a baby, Ben (Rogen) and Allison (Heigl) accidentally get pregnant after a one-night stand and attempt to give the relationship a chance.

It takes a frank look at how two very different people can make a romance work.

Knocked Up doesn’t try to moralize the story or push back on Allison and Ben’s decisions and lives. Instead, it takes a frank look at how two very different people can make a romance work. The movie works so well because it’s committed to realism, juxtaposing Ben and Allison’s relationship with the struggling marriage of Allison’s sister and admitting that things don’t always work out. Though Knocked Up has faced some criticism, it’s overwhelmingly fun to watch.

4

Game Night (2018)

Directed by John Francis Daley & Jonathan Goldstein

Though the concept of Game Night is hilarious enough on its own, it’s the performances that take the action-comedy to the next level. Taking an ordinary game night and raising the stakes so that the characters are actually fighting for their lives immediately subverts the audience’s expectations and creates opportunities for intrigue and adventure. Jason Bateman and Rachel McAdams are up for anything as they tackle the ups and downs of their unexpected evening.

The scene-stealer of Game Night, Jesse Plemons, embodies the humor that makes the movie so fun, as he takes his role seriously, even when his character and the circumstances are ridiculous. Balancing such intense stakes and tension with such a strong sense of fun and self-awareness sets Game Night apart from similar projects. A lesser movie would collapse under the weight of the plot-heavy story, but Game Night never wastes an opportunity to find a laugh.

3

Superbad (2007)

Directed by Greg Mottola

While there are many additions to the teen comedy genre that see a group of uncool friends attempt to make the most out of their high school careers in one wild night, few are as good as Superbad​​​​​​. Boasting a terrific cast led by Michael Cera and Jonah Hill, Superbad is a time capsule of what it was like to be in high school and a comedian in the early 2000s while still being relatable and funny today. Superbad easily balances its sense of humor with a strong sense of story and character through Seth (Hill) and Evan’s (Cera) dynamic.

Superbad has inspired many comedy films since its premiere, and the influence it’s had on not just the teen genre but comedy in general. As time has progressed, Superbad has retained its relevance and popularity and has been recognized as a great example of how the single-day movie has evolved in the modern era. For viewers experiencing Superbad for the first time, there’s nothing more exciting than experiencing the iconic story and seeing how it connects to the world of comedy.

2

Zack And Miri Make A Porno (2008)

Directed by Kevin Smith

Despite the explicit name and content of the film Zack and Miri Make a Porno, this Sєx comedy is one of the most romantic and heartfelt additions to the R-rated comedy genre. What starts as an attempt to make some quick cash by making an adult film soon spirals out of control and helps the тιтle characters realize their feelings for each other. Elizabeth Banks and Seth Rogen have a sweet, genuine connection on screen, making it easy to believe that Zack and Miri would start to fall in love.

It’s easy to be surprised by how innocent and vulnerable the performances in the movie are, but this is what makes it so charming.

The director, Kevin Smith, is well known for his funny yet heartfelt contributions to the comedy genre, like Clerks, and his style, coupled with Banks’ and Rogen’s chemistry, is the perfect combination. As time has progressed, Zack and Miri Make a Porno has become more popular and better remembered, as even its most risqué jokes are told in good fun. It’s easy to be surprised by how innocent and vulnerable the performances in the movie are, but this is what makes it so charming.

1

Bridesmaids (2011)

Directed by Paul Feig

The ensemble cast of Bridesmaids is a large part of what has allowed the 2011 comedy to age so well and still be remembered as one of the greatest comedies of the 2010s. Kristen Wiig and Maya Rudolph have amazing chemistry as Annie and Lillian, the best friends the film follows, and it can’t be ignored that Bridesmaids has been a crucial movie that has helped pave the way for more female-led R-rated comedies. In such a male-dominated field, Bridesmaids easily rises to the top in humor and emotional impact.

It never gets old to revisit Bridesmaids and accompany Annie and Lillian on the many misadventures and misfortunes that follow them. Poking fun at the tropes and stereotypes surrounding female friendships as well as the intense rituals of weddings and marriage, Bridesmaids instantly connects with its audience and appeals to everyone who watches it. Bridesmaids will be remembered as a benchmark for comedy filmmaking for years to come in terms of performance, writing, and genuinely funny moments that land today.