'America's Sweethearts' 20th anniversary: Best 2000s rom-coms to stream

Twenty years ago on July 20, 2001, Julia Roberts, Catherine Zeta-Jones, John Cusack and Billy Crystal’s quirky rom-com “America’s Sweethearts” hit theaters — and now you can stream it anytime on Showtime or HBO Max. In the movie stacked with A-listers, Catherine and John play Gwen Harrison and Eddie Thomas, beloved husband-and-wife movie stars who’ve secretly split up while making a film together with an eccentric director. Billy’s publicist character, Lee, and Julia, who plays Gwen’s sister and assistant, maneuver to hide the truth from the press and get the exes back together for the junket so the film can be a success — but nothing quite goes to plan. In honor of the movie’s milestone anniversary, Wonderwall.com is rounding up our favorite rom-coms of the ’00s and letting you know where you can currently stream them.

Keep reading to see if your favorite aughts romance made the list…

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2001 was a great year for rom-coms! It’s also the year “The Wedding Planner” — starring the one and only Matthew McConaughey alongside Jennifer Lopez as wedding planner Mary Fiore — came out. Mary falls for Matthew’s character, pediatrician Steve “Eddie” Edison, without knowing he’s actually one of her clients (in a perfect rom-com meet-cute where he saves her from getting slammed by a runaway dumpster when her Gucci heel gets stuck in a grate), all while her father is pushing her to settle down with family friend Massimo (Justin Chambers). This classic is streaming now on Peacock.

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“How to Lose a Guy in 10 Days” is the quintessential ’00s rom-com — from the killer soundtrack with that Keith Urban classic (“Somebody Like You”) to Matthew McConaughey in his prime. Kate Hudson’s character, Andie Anderson, works at a women’s magazine and in a quest to write an article called, well, “How to Lose a Guy in 10 Days,” sets out to rid herself of a new beau (Matthew) in this adorable 2003 flick. She doesn’t know that the object of her affection, Benjamin Barry, is an ad exec trying to make the next woman he comes across fall madly in love with him for his own wager at work, leaving hilarity to ensue. Rent or buy this one on Amazon Prime Video or the iTunes Store.

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The late ’00s brought us this next great pick, 2008’s “Forgetting Sarah Marshall.” This one starring Jason Segel chronicles his character Peter’s relationship with actress Sarah Marshall (Kristen Bell) and their subsequent breakup, which eventually leads them both to the same resort in Hawaii where she’s vacationing with her new boyfriend, rocker Aldous Snow (Russell Brand). But you don’t have to feel too bad for Peter… he ends up hitting it off with resort receptionist Rachel (Mila Kunis). Starz has this flick streaming anytime.

The ’00s were filled with great teen rom-coms as well — like 2006’s “She’s the Man,” which starred Amanda Bynes and Channing Tatum. The comedy, which was inspired by “Twelfth Night” by Shakespeare, saw Amanda as Viola Hastings, a teen posing as her twin brother so she can play on the boys soccer team at his new prep school after the girls’ team gets cut. Channing plays the team’s resident hot captain, Duke, who Viola’s alter-ego promises to help unite with his crush, Olivia. Instead, Viola ends up falling for Duke, hard, only to eventually share the truth about her identity. Buy or rent this one in the iTunes Store or Vudu anytime.

Reese Witherspoon’s next great rom-com of the ’00s came out in 2002 — “Sweet Home Alabama.” She starred as fashion designer Melanie Carmichael, who’s primed to marry Andrew Hennings (Patrick Dempsey), the son of New York City’s mayor, but finds herself in a love triangle after returning to her small Southern hometown to quietly finalize her divorce from childhood pal Jake (Josh Lucas). Rent or buy it on Amazon Prime Video, the iTunes Store or Vudu tonight.

“Legally Blonde” is much more than a rom-com, of course, but we’d be remiss to not include this ’00s classic. The film, which hit theaters in 2001, shows Reese Witherspoon’s most iconic character, Elle Woods, navigating an aesthetically pleasing path to Harvard Law School, in which she enrolls to win back her ex, Warner Huntington III (Matthew Davis), but instead finds independence, a future career and love with older lawyer Emmett (Luke Wilson). Watch it on Netflix, Amazon Instant Video, Google Play, Vudu and more.

Debra Messing stepped into a rom-com leading lady role in 2005’s “The Wedding Date.” The film saw her play Kat, a single woman from New York serving as the maid of honor at her sister’s wedding where her ex will be the best man. She hires a hunky escort named Nick (Dermot Mulroney) to pretend to be her boyfriend for the wedding festivities and ends up — what else?! — actually falling for him. Amazon Prime Video, the iTunes Store and Vudu all have this film to rent or buy.

It was about time Will Smith did a rom-com! His 2005 flick “Hitch” co-starred Eva Mendes. Will played Alex “Hitch” Hitchens, a professional dating coach who crosses paths with gossip columnist Sara (Eva) and discovers none of his tricks work on her. It’s available to rent or buy on Amazon Prime Video, the iTunes Store or Vudu.

“Serendipity,” which came out in 2001, chronicled the love story between Sarah and Jonathan (played by Kate Beckinsale and John Cusack, respectively). The duo spend one fateful night together, only to attempt to reconnect more than a decade later back in New York City. Despite frustrating near misses, eventually, these two find their way back to each other for a happy ending — which you can watch on HBO Max anytime!

2004’s “13 Going on 30” saw Jennifer Garner’s character, Jenna Rink, navigating the high-stakes work of women’s magazine publishing as a 13-year-old girl trapped in a 30-year-old woman’s body. Aside from the obvious laughs, it also featured a sweet time-traveling romance with Mark Ruffalo’s character, Matt, her childhood best friend. Watch it on HBO Max, the iTunes Store and more.

The classic Cinderella tale got an updated twist in 2004’s “A Cinderella Story” starring ’00s superstars Hilary Duff and Chad Michael Murray. The fairy tale was brought to the present day, with the high schoolers falling in love online anonymously. Catch this one streaming on HBO Max.

One of the best rom-coms of the ’00s? “My Big Fat Greek Wedding,” which was such a big hit after its 2002 release that it became the highest grossing rom-com in film history at the time. It starred Nia Vardalos as Toula, a woman living at home and working at her tight-knit Greek family’s businesses when she meets a non-Greek customer, Ian Miller (John Corbett), and falls in love with him. The laughs come in as they try to plan a traditional Greek wedding but the couple’s sweet romance takes center stage. Stream it on HBO Max.

2004 brought us “50 First Dates,” a romantic comedy that united funny stars Adam Sandler and Drew Barrymore. Adam’s character, Henry, is a marine veterinarian (gotta love rom-com jobs!) who falls for Drew’s character, Lucy, an art teacher who has amnesia and forgets him daily. Henry must win her over day after day as their relationship ensues. You can stream this movie anytime on AMC.

Ryan Reynolds and Sandra Bullock teamed up for 2009’s “The Proposal.” This rom-com centered around a Canadian executive risking deportation due to an expired visa (Sandra’s Margaret) who talks her assistant into pretending to be her fiancé (Ryan’s Andrew). Reminisce and rent or buy this flick on Amazon Prime Video, the iTunes Store or Vudu.

“27 Dresses” came out in 2008 and starred Katherine Heigl as Jane, a woman who was always a bridesmaid (27 times!) and never a bride. She ends up bumping into fellow wedding skeptic Kevin (James Marsden) while juggling bridesmaid duties in two weddings. The journalist sets out to write a piece about her being a “perpetual bridesmaid” before he eventually falls for her. HBO Max has this one streaming now.  

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