You may have noticed a handful of newly arrived rom-coms on HBO Max have one thing in common: Steve Carell.
This was probably planned because Carell is starring in HBO’s new original comedy Rooster. But he does have impressive cred in romantic comedies.
We’ve narrowed down this month’s options to two of Carell’s rom-coms: The 40-Year-Old Virgin and Crazy, Stupid, Love.
You can find both of those films and more among the Watch With Us team’s picks for the must-watch rom-coms on HBO Max.
It may sound strange to say, but Steve Carell is The 40-Year-Old Virgin. Or rather, his character, Andy Stitzer, is a virgin, much to his chagrin. Once Andy’s friends, David (Paul Rudd), Jay (Romany Malco) and Cal (Seth Rogen) figure that out, they do everything they can to help him break that streak.
Andy’s best chance to find love with a woman is Trish Piedmont (Catherine Keener), a single mother who seems really taken with him. But Andy’s hangups about sex are more than one or even 20 dates can fix.
The 40-Year-Old Virgin is streaming on HBO Max.
Crazy, Stupid, Love. features Steve Carell as Cal Weaver, a man who can’t deal with the fact that his wife, Emily (Julianne Moore), is leaving him for someone else. However, Cal makes a big change in his life when his new friend, Jacob Palmer (Ryan Gosling), teaches him how to pick up women.
What neither Cal or Jacob know is that the latter’s latest girlfriend, Hannah (Emma Stone), is Cal’s grown daughter. That throws their friendship into a spiral just as Cal decides he wants to win back Emily’s heart.
Crazy, Stupid, Love. is streaming on HBO Max.
Two decades ago, Jennifer Lopez and Jane Fonda had an epic generational clash in Monster-in Law. Lopez plays Charlotte “Charlie” Cantilini, a woman who is head-over-heels in love with Kevin Fields (Michael Vartan). But as the couple begins preparations to get married, Kevin’s mother, Viola Fields (Fonda), decides that Charlie isn’t good enough for her son.
Viola is going through a rough patch in her life, but that doesn’t excuse the Hell she unleashes on Charlie as she tries to break up the happy couple. There’s only room for one woman in Kevin’s life, and his mom is determined to do anything to make sure it isn’t Charlie.
Monster-in-Law is streaming on HBO Max.
2 Days in New York is a sequel to 2 Days in Paris, but you don’t need to have seen the first film to enjoy this one. All you need to know is that director, cowriter and star Julie Delpy is back, and her character, Marion, is in a happy relationship with Mingus Robinson (Chris Rock) as their blended family lives together in New York.
Unfortunately for the couple, Marion’s father, Jeannot (Albert Delphy), her sister, Rose (Alexia Landeau), and Rose’s boyfriend, Manu (Alex Nahon), are all in town to meet Mingus. That trio leaves a lot of chaos in their wake, especially Rose, who seems to be going out of her way to try to get Mingus’ romantic attention. There’s only so much Marion can do before the entire situation unravels.
2 Days in New York is streaming on HBO Max.
Jason Bateman and Jennifer Aniston play best friends Wally Mars and Kassie Larson in The Switch. But Wally may not be as good a friend as he should be, in part because he’s still harboring a torch for Kassie. When she declares her intention to have a child, Wally drunkenly destroys her donor’s sample and replaces it with his own.
Seven years later, Kassie has a son, Sebastian (Thomas Robinson), who resembles Wally in ways that are more than just physical. Kassie is also dating Roland Nilson (Patrick Wilson), the man she believes to be her son’s father. After bonding with Sebastian, Wally realizes what he’s done and tries to reconcile his feelings for Kassie before it’s too late.
The Switch is streaming on HBO Max.
It doesn’t take Erin Langford (Drew Barrymore) and Garrett Scully (Justin Long) to get together in Going the Distance. These two were practically made for each other and they can barely keep their hands to themselves. The only problem is they live in cities that are hundreds of miles apart. Regardless, they decide to give a long-distance relationship a try.
Despite the apparent love between them, things don’t quite go how they hoped. Erin and Garrett think they know what they want out of life and from each other. But when potential career breakthroughs are offered, this couple may not be able to make it on love alone.
Going the Distance is streaming on HBO Max.
Owen Wilson and Vince Vaughn‘s Wedding Crashers is one of the duo’s most famous movies. In this comedy classic, they play divorce mediators John Beckwith (Wilson) and Jeremy Grey (Vaughn), a pair of best friends who have perfected the art of dropping in on other people’s weddings and picking up single women. This time, Jeremy has snagged Gloria Cleary (Isla Fisher), while John is very attracted to her sister, Claire (Rachel McAdams).
Unfortunately for John, Claire already has a boyfriend, Sack Lodge (Bradley Cooper), and he’s ruthless about keeping away any potential rivals. John and Jeremy are also using false identities, and their continued presence in the lives of the Cleary family threatens to expose their lies to the women they desire.
Wedding Crashers is streaming on HBO Max.
We live in very cynical times, and Lucy Mason (Dakota Johnson) has embraced that in Materialists. Lucy’s been a failure in love and as an actress, but she’s found her calling as a matchmaker who helps women find financially successful men to date and potentially marry. She’s so good at her job that a very wealthy man, Harry Castillo (Pedro Pascal), starts courting her himself.
At the same time, Lucy reconnects with her ex-boyfriend, John Pitts (Chris Evans), a struggling actor who can’t give Lucy the life of luxury that she wants. That’s not a problem for Harry, but Lucy will eventually have to decide what’s really important to her: Love or money?
Materialists is streaming on HBO Max.
If you don’t remember seeing Starter for 10 in theaters nearly two decades ago, it’s probably because it wasn’t widely seen in America. But the film has a loaded cast including Benedict Cumberbatch, Dominic Cooper, James Corden, Rebecca Hall, Alice Eve and one of the first leading roles for James McAvoy.
McAvoy portrays Brian Jackson, a college student who is eager to take part in the TV quiz show University Challenge. Brian is so attracted to one of his teammates, Alice Harbinson (Eve), that he nearly gives up his opportunity on the team for her. After being rejected, Brian finds himself drawn to another student, Rebecca Epstein (Hall), but his lingering feelings for Alice may cause him to lose both women.
Starter for 10 is streaming on HBO Max.
Usually, rom-coms save any weddings for the end of the movie. I Give It a Year bucks that trend by having a wedding near the beginning of the film, because Nat Redfern (Rose Byrne) and Joss Moss (Rafe Spall) are just smitten with each other.
Unfortunately for the pair, the honeymoon phase doesn’t last long, and their pronounced differences make them question their choice to get married. Complicating matters include Joss’ lingering affection for his ex-girlfriend, Chloe (Anna Faris), and Nat’s increasing desire for her client, Guy Harrap (Simon Baker). If Nat and Josh can’t work out their issues, their marriage is going to end very badly.
I Give It a Year is streaming on HBO Max.
Singing’ in the Rain wasn’t an immediate sensation in 1952, but it’s now widely regarded as one of the greatest movies ever made. The story takes place nearly a century ago in Hollywood, as silent pictures are about to go the way of the dodo. Movie star Don Lockwood (Gene Kelly) is afraid his career will go with it.
Although Don is romantically linked by the press to his costar, Lina Lamont (Jean Hagen), he falls head over heels for a novice actress, Kathy Selden (Debbie Reynolds). It’s the kind of love that just makes you want to sing in the rain, apparently. But if Lina has her way, she’ll keep Don and Kathy apart. The music is incredibly catchy, and that’s a big reason why this film feels timeless.
Singin’ in the Rain is streaming on HBO Max.
This Broadway adaptation of the Keri Russell romantic dramedy has even more delicious heart than the original. When diner waitress and master pie baker Jenna (Sara Bareilles, who also wrote the music for the show) finds herself pregnant, she decides to save up and enter a pie contest to escape her abusive husband Earl (Joe Tippett). Her best friends Dawn (Caitlin Houlahan) and Becky (Charity Angél Dawson) encourage her along the way. But things get a little more complicated when, much to her surprise, she ends up having an affair with her kind and understanding OB/GYN, Dr. Pomatter (Drew Gehling).
Jenna’s pregnancy helps her discover the strength she never imagined she had. The songs are irresistibly funny and catchy in one moment and heartbreakingly beautiful in the next. Waitress: The Musical will leave you hungry for more — and for a slice of pie.
Waitress: The Musical is streaming on HBO Max.
Toula (Nia Vardalos) is a shy, awkward woman who has always felt like an outsider in her loud, effusive Greek American family. When she falls in love with WASP-y teacher Ian (John Corbett), she struggles to get her family to accept him. Throughout the movie, she learns to stand up for herself and the man she loves, but she also learns to appreciate the rich culture that makes her family unique. It’s a heartwarming, hilarious story.
Despite being over twenty years old, My Big Fat Greek Wedding remains the highest-grossing rom-com of all time — and rightfully so. The script, written by lead actress Vardalos, is instantly quotable and emotionally resonant. More importantly, Toula and Ian’s romance is endlessly endearing. The movie spawned two sequels in 2016 and 2023, but the original remains the best of the bunch.
My Big Fat Greek Wedding is streaming on HBO Max.
