Sex comedies are a sub-genre of comedy films that have been around for a long time, evolving through the ages from 1959's Some Like It Hot to classics like Fast Times at Ridgemont High of the late '90s and '80s era. The popularity of the genre continues throughout the 2000s, and one of the most popular and best to come out of this period is The 40-Year-Old Virgin, starring The Office star, Steve Carell. Its premise was outlandish and one that had never been done before and it produced some hilarious results.
But the film is not just a comedy about a man in his 40s trying to lose his virginity, but more about a group of friends coming together and a man learning about who he is as he moves outside his comfort zone and falls in love. The combination of heart and humor in The 40-Year-Old Virgin is a rare one, and the following films come closer than most to capturing that same feeling.
The To Do List (2013) - Available On Fubo & Showtime
Teenager Brandy Klark is no Andy Stitzer and nor is she 40 years old, but the peer pressure that is put on her to have sex is the same as in The 40-Year-Old Virgin. Eventually, she gets annoyed by all the ostracism from people her age and decides to lose her virginity, and even finds a candidate for the event.
With Parks and Recreation star Aubrey Plaza in the lead, The To Do List features some hilarious acting from some popular comedy actors such as Bill Hader, Andy Samberg, and Donald Glover.
Sleeping With Other People (2015) - Available On AMC
The main characters in Sleeping With Other People have the exact opposite dilemma of what happens in The 40-Year-Old Virgin. Lainey and Jake are two people whose addiction to sex is causing problems in their social lives and ability to maintain romantic attachments.
What begins as a typical rom-com about two people, just like some of the other best and worst rom-coms of the 2010s, evolves into something much more emotionally mature by the end of the story, as they try to ignore their feelings for each other for the sake of the people around them.
Two Night Stand (2014) - Available On Amazon Prime
Much to the chagrin of her roommates, Megan does nothing much and lazes around all day long, being unemployed on top of being single. She has a one-night stand with someone she meets through a dating website, which doesn't go as well as expected.
To make matters worse, the two of them are stuck together inside the same house due to an ongoing blizzard outside. With no option other than to tolerate each other's company, they eventually end up growing closer. Two Night Stand tries to explore the complexity of physical relationships (or the lack thereof) in the same way The 40 Year Old Virgin does.
The Night Before (2015) - Available On Fubo
Three friends: Isaac, Isaac, and Chris, have maintained the tradition of going out to party together on Christmas eve for many years, but one they feel the need to end due to their growing personal responsibilities. The three of them seek out the legendary Nutcracker Ball party, which is deemed to be the most exclusive party in all of New York.
Fans of 40-Year-Old Virgin should make an effort to check out Seth Rogen's other best films, and The Night Before is another great ensemble effort. They all carry a similar humorous atmosphere that is great for a casual viewing experience.
That Awkward Moment (2014) - Available To Rent On Amazon, YouTube & More
That Awkward Moment revolves around three best friends living in New York City and their various romantic correspondence with various women. It's not the best of its genre, but the chemistry between the lead stars Zac Efron, Miles Teller, and Michael B. Jordan is what makes it worthwhile.
Some of the funniest scenes in The 40-Year-Old Virgin are a product of when the lead characters are goofing around, and That Awkward Moment shares much of the same type of playfulness.
Superbad (2007) - Available On Netflix
The tendency among teenagers to overvalue the importance of losing one's virginity is a commonly seen theme in all kinds of teen movies or shows. Teenagers Seth and Evan, played by The Wolf of Wall Street actor Jonah Hill and Arrested Development star Michael Cera, are at the center of this foul-mouthed but full-of-heart teen comedy that is one of the movies that gets a few things right about being a teenager.
The boys in Superbad act like complete goofballs and are obsessed with sex in the same way that the men in The 40-Year-Old Virgin are, but at least they are acting their age. Soon going to separate colleges, these two childhood friends decide to go all out for a party where they are hoping to get lucky with their respective romantic interests.
Crazy, Stupid, Love (2011) - Available On Netflix
With the same lead star Steve Carell in a very similar role, but not ranked as one of his best roles according to Metacritic, no other movie is possibly more like The 40-Year-Old Virgin. In Crazy, Stupid Love, he plays a middle-aged man Cal Weaver, whose wife tells him she is cheating on him, leading to a divorce.
Cal now spends his empty nights at a club, where a bonafide philanderer, Jacob Palmer (played perfectly by Ryan Gosling) takes him in and teaches him how to be a better version of himself.
I Love You, Man (2009) - Available On Paramount+
While The 40-Year-Old Virgin is about a man being helped by his friends in his quest for a girlfriend, I Love You, Man is about a guy whose girlfriend wants him to find a good guy friend. Real estate agent Peter Klaven doesn't have a single male friend.
Now that his wedding is coming up, he must find someone suitable to befriend so that they can fill in for the role of best man.
Forgetting Sarah Marshall (2011) - Available On Amazon Prime
After getting dumped by his girlfriend of five years, Peter Bretter comes to the conclusion that what he needs to do to move on with his life is to go on a solo vacation to Hawaii. By a twist of fate, he arrives at his chosen Hawaiian resort only to discover that his ex-girlfriend, the titular Sarah Marshall, is also staying there with her new boyfriend.
Forgetting Sarah Marshall was produced by The 40-Year-Old Virgin director Judd Apatow, a name that is synonymous with the funniest comedies, so there is plenty of reason for The 40-Year-Old Virgin to check it out.
40 Days And 40 Nights (2002) - Available On HBO Max
After going through a particularly bad break-up, Matt Sullivan finds himself struggling to enjoy the company of others. As the time for the Christian religious event, Lent, approaches, he decides to take a vow of celibacy for 40 days, which will mean he will have to refrain from all kinds of sexual activities.
Similarities in the title aside, viewers may find it funny to see how Matt struggles to maintain his vow for only 40 days, while comparatively, The 40-Year-Old Virgin's Andy Stitzer made it through 40 years. With a 39% rating on Rotten Tomatoes, this sex-comedy from the director of the cult-classic black-comedy film, Heathers, (a movie that holds up but didn't entirely age well), wasn't exactly met with critical acclaim, but it's definitely worth checking out for fans of The 40-Year-Old Virgin.