Movies like Pyrates (1991)
The best movies like Pyrates (1991) are How to Please a Woman (2022), XX/XY (2002) and The Best You Can (2025). If Pyrates hooked you with its romance and comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRosaline (2022)7.1/10 from 346 votes
- NewestWhy Did I Get Married Again? (2026)Released 2026
How to Please a Woman (2022)
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisXX/XY (2002)
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisStrictly Sexual (2008)
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisYoung People Fucking (2007)
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisRosaline (2022)
Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisSitting in Bars with Cake (2023)
Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisDirty Sexy Saint (2019)
Clay Kincaid hates the nickname 'Saint', he got for being too kind to stray animals and desperate people. Especially when it comes to women. With a rough and damaged past that has left him jaded, he doesn't do committed relationships. This is before he meets Samantha Jamieson, an heiress turned runaway in need of help. When she starts to work as a waitress at his bar, he discovers that she is someone truly special and amazing… someone that could warm his damaged heart.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisThe Good House (2021)
When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person she's been avoiding for decades: herself. Based on the best-selling novel by Ann Leary.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like this(Untitled) (2009)
A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisDelirious (2007)
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisNumb (2007)
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisLove & Sex (2000)
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWhy Did I Get Married Again? (2026)
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNight Owls (2015)
After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills, Kevin is forced to keep her awake... and over the course of the night the two begin to fall for each other.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisThe Giant Mechanical Man (2012)
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like this
Like Pyrates and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Pyrates?
The closest matches to Pyrates are How to Please a Woman (2022), XX/XY (2002) and The Best You Can (2025). Below are 17 more, each with the reason it matches.
What should I watch after Pyrates?
Start with How to Please a Woman (2022), the closest match to Pyrates.
What is the highest-rated movie like Pyrates?
Rosaline (2022), rated 7.1/10 by 346 TMDB users.
What is the newest movie like Pyrates?
Why Did I Get Married Again? (2026) is the most recent release on this list.
Are there English movies like Pyrates?
Yes: How to Please a Woman (2022), XX/XY (2002) and The Best You Can (2025).
How are movies similar to Pyrates chosen?
First come films that Trakt’s viewers watch alongside Pyrates, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.