February may be over, but love endures all seasons.
We don’t know about you, but the Watch With Us team is a huge fan of romantic comedies.
The enduring charm of When Harry Met Sally, the lasting humor of Clueless, the infectious wit of Hit Man — the best rom-coms always make you feel good, and we can’t get enough of them.
This March, Watch With Us has rounded up our four picks for rom-com movie masterpieces, and where you can watch them.
Our first choice is the timeless masterpiece Annie Hall, starring the late Diane Keaton.
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‘Annie Hall’ (1977) — Tubi
New York comedian Alvy Singer (Woody Allen) reflects on how it all went wrong with his ex-girlfriend, aspiring nightclub singer Annie Hall (Diane Keaton), in this funny, moving rom-com masterpiece. Annie Hall follows Alvy as he examines both his tumultuous relationship with Annie as well as his childhood growing up in Brooklyn, as he breaks the fourth wall, speaking directly to the audience while alternating between different periods of time to paint a full portrait of how he and Annie met and where they ended up. To illustrate how the two struggled through the many obstacles of modern romance, surreal fantasy sequences are blended with intimate moments of character drama.
Hilarious and devastating in equal measure, Annie Hall remains one of the best romantic comedies of all time, even now, almost 50 years since it came out. The superb, incisive screenwriting, tender lead performances (in particular, a career-defining turn from Keaton that remains arguably the best performance of her whole impressive oeuvre) and confident blending of profound introspection and intense joy work together to make Annie Hall a masterpiece that reinvigorates every time you revisit it.
‘It’s Complicated’ (2009) — HBO Max
Bakery owner Jane (Meryl Streep) and successful attorney Jake (Alec Baldwin) have been divorced from one another for ten years, yet they have managed to remain good friends while caring for the three children they share together. Though Jake got remarried to the much younger woman (Lake Bell) with whom he cheated on Jane, Jane ends up being Jake’s new “other woman.” While out having drinks one-on-one following their son’s graduation, Jake and Jane unexpectedly end up sleeping together. Thus, the two exes pursue a steamy yet unconventional affair, while Jane’s new architect, Adam (Steve Martin), quietly falls for her.
It’s Complicated is a perfect Nancy Meyers rom-com, with the cozy atmosphere and aspirational aesthetics typical of Meyers’ productions, married (no pun intended) to some believable and warm-hearted chemistry between Baldwin and Streep. The mature storytelling blends laugh-out-loud humor with realistic and relatable situations. It’s refreshing the way that It’s Complicated tackles an affair between two older people, offering audiences something different than the typical young love story.
‘Moonstruck’ (1987) — Peacock
Though Italian American Loretta Castorini (Cher) is betrothed to the much older Johnny Cammareri (Danny Aiello), she isn’t without second thoughts. Still, as a woman already about to be on her second marriage, Loretta feels like she just has to take what she can get. But while Johnny is away in Sicily tending to his dying mother, Loretta ends up meeting Johnny’s estranged younger brother, the hot-headed Ronny (Nicolas Cage) — and she falls for his melodramatic passion almost instantly. As Loretta falls harder for Ronny, she realizes she is going to have to make a crucial decision.
Moonstruck garnered the iconic Cher her first Academy Award, and it’s her charismatic performance that helps to guide the film to being a chaotic and hilarious romance movie. Of course, Cher’s portrayal of Loretta wouldn’t be what it is without the chemistry she shares with Cage, whose hair-trigger personality provides an endearing “opposites attract” angle to their dynamic. The movie is an enduring celebration of messy, imperfect love.
‘There’s Something About Mary’ (1998) — Hulu
In 1985, Ted Stroehmann (Ben Stiller) is set to take his dream girl, Mary Jensen (Cameron Diaz), to the prom, but an embarrassing incident in her bathroom prevents him from going, and he loses contact with her. Years later, viewing Mary as “the one who got away,” Ted hires private detective Pat Healy (Matt Dillon) to find her so he can finally get a second chance. But when Pat finds Mary, he falls for her too and purposefully gives Ted false information. Deciding to find her himself, Ted ends up having to dodge both Pat and yet another suitor who finds Mary’s charms utterly irresistible.
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There’s Something About Mary somehow manages to weave juvenile humor that’s actually funny with an emotional core that’s actually affecting. The film succeeds in this delicate balance between gross-out gags and outrageousness and a sweet romantic heart, proving that tender love stories can also feature some of the dumbest and silliest humor you’ve ever been exposed to. There is never a dull moment in the script, with Dillon delivering a hilarious performance that proves that the Drugstore Cowboy actor has some nimble comedic chops.
