Sandra Bullock’s 10 Best Romance Movies, Ranked

Did you remember that Bullock and Ben Affleck starred in a road trip rom-com from 1999, where a bird flies into the engine of their plane, the two strangers rent a car to get to Savannah for his wedding, and get trapped in a K-Mart during a rainstorm? It’s OK if you don’t because, in the banner year of movies that was 1999, this is a forgotten deep cut. Like with most of Bullock’s other imperfect films, this one still has its moments, thanks to her winning commitment (and who didn’t want to let loose in a department store in the ’90s). And spoiler alert for 25 years ago: it has a rare happy ending where the two leads don’t get together.

Perhaps the most straight-forward romantic comedy she has ever made, Bullock stars in this enemies-to-lovers story about an idealistic New York City lawyer who clashes with and eventually falls for her arrogant billionaire playboy boss (Hugh Grant). The charms of its leads are what saves this by-the-book movie, but who cares? It would have felt wrong if Bullock and Grant never shared the screen! If you are going to revisit it, just be warned: there is a cameo from Donald Trump because if any movie talked about the New York City real estate market in 2002, it likely had a cameo from the former president. Hopefully that saves you a jump scare.

Reuniting with her Speed co-star Keanu Reeves, the pair pivoted from action romance to time-traveling epic with this story about two pen pals living in the same lake house two years apart. They communicate through a magical mailbox that proves even time can’t stop a good love story. While not as thrilling or coherent as Speed, the chemistry between Bullock and Reeves is undeniable no matter the situation. This slow-burn romance was a nice change of pace after their high-energy first outing. (Bonus: look out for The Bear’s Ebon Moss-Bachrach as Reeves’ younger brother!)

Bullock’s return to the action romance genre was a huge hit that reminded Hollywood that audiences do love these kinds of movies, especially when they are led by Bullock. It follows Loretta Sage (Bullock), a romance novelist taken hostage by a treasure hunter (Daniel Radcliffe), who believes her background as an archaeologist means she can help him locate a priceless crown on an island. Loretta’s only hope for survival is the last person she wants to see: Alan (Channing Tatum), the somewhat-dim cover model for all of her books. Bullock and Tatum are a dynamite pair in this, and, no, that is not a joke about all the dynamite denoted by Brad Pitt in his cameo scene.

Nothing says a ’90s movie like getting ambushed by your cheating husband as a guest on a Sally Jessy Raphael-type daytime talk show, and that’s what happens to poor Birdee Calvert. Unable to escape the nationally televised heartbreak, Birdee and her young daughter Bernice move back to her Texas hometown where she comes to terms with being a mother and a daughter, while also falling into a romance with a completely dreamy Harry Connick Jr. She also works at Kodak photo printing shop, if you need to be reminded it was the ’90s. A melodrama of the highest order, Bullock is utterly heartwarming in this Forest Whitaker-directed movie that co-stars Gena Rowlands and a young Mae Whitman.

FBI Agent Gracie Hart’s longest relationship has been with her gun, until she is enlisted in an elaborate undercover operation to infiltrate the Miss United States pageant and thwart a terrorist attack from the inside. After a makeover from renowned pageant coach Victor Melling (Michael Caine) and some quality time with her fellow contestants, Gracie’s prejudice against the prim and proper world of pageants begins to soften. While she is beauty and she is grace, New Jersey’s Gracie Lou Freebush is not the next Miss United States. But she is one of Bullock’s greatest characters, and her relationship with her disarmingly handsome fellow agent played by Benjamin Bratt isn’t bad either.

One of Bullock’s most popular movies (which is getting a sequel 26 years later!) isn’t a love story between a man and a woman. It is the enduring love story between two sisters, Sally (Bullock) and Gillian (Nicole Kidman), who also happen to be witches. While Sally focused on raising a family, Gillian spent her 20s traveling the world with various paramours. But a blood bond they shared as teenagers forever brings them back to one another, especially after a family curse kills Sally’s husband and the pair accidentally kill Gillian’s abusive boyfriend. Sisterhood, covens, and PTA phone trees were just a few of the circles of love in this autumnal favorite. Bullock’s second chance at love with Aiden Quinn’s detective also gives the story some romantic tension.

While Speed is not explicitly a romantic movie, who are we kidding? Was there anything more romantic than Keanu Reeves holding on tight to Bullock as they slid out from under that bus with literal sparks flying around them from metal grinding on the asphalt? The answer is no. The kiss they shared at the end of it just sealed the deal that, more than most, Bullock has a knack for marrying the heart-pounding fun of action with the heart-swelling thrill of romance. Oh, and here’s an unpopular but correct opinion—Speed 2: Cruise Control isn’t that bad!

In 2009, Bullock released three movies. The Blind Side, for which she won her Oscar. The better-off-forgotten All About Steve, for which she definitely didn’t win an Oscar. And The Proposal, with which she set the box office on fire. Of the three, it is the most fondly remembered movie and an all-time great chemistry pairing with Ryan Reynolds. Bullock starred as publishing executive Margaret Tate, a Canadian-born citizen whose expiring visa leads to a desperate ploy where she pretends to be the fiancé of her overworked assistant (Reynolds) to get a green card. The two travel to his hometown in Alaska to give the sham some legitimacy, interacting with his family (including Mary Steenburgen and Craig T. Nelson). Bullock has never been better as Margaret’s cold-hearted priorities start to melt in the Alaskan sun, even going so far as to release her negative energy in a hysterical bonfire ritual scene with the movie’s MVP, Betty White.

Before the pressures of Hollywood expectations were put on her shoulders, this cozy, Christmastime-set movie made chunky sweaters a fashion statement and Bullock a star. As the instantly likable Lucy Eleanor Moderatz, Bullock turned a lonely Chicago transit worker into the kind of relatable and empathetic heroine that defined this era of ’90s romances. When Lucy saves the life of a daily commuter (Peter Gallagher) who she also has a crush on, his family mistakes her for his fiancé, and she goes along with it—until she meets his brother (Bill Pullman). A tender-hearted comedy about the little misunderstandings that snowball into life-changing shenanigans, While You Were Sleeping is among the most rewatchable movies you will find, and it is because Bullock is just so good at being someone to root for and fall in love with—even if she’s already got her hands full with two brothers.