Two If By Sea
Apologies to Denis Leary, Bullock's leading man who co-wrote this 1996 box office bomb, but we literally did not even know it existed until scrolling her Wikipedia page. And the 13 percent rating it currently holds on Rotten Tomatoes did not inspire us to find it on a streaming service either.
All About Steve
Well, at least this absolute stinker that paired Bullock with Bradley Cooper helped its star make history as the first actor to win an Oscar (for The Blind Side) and a Razzie in the same year in 2009? And, just to prove once again how cool she is, Bullock showed up in-person to accept the dishonor. We stan a self-deprecating queen!
Forces of Nature
While we love the upending of the happily ever after trope—Spoiler: they do not end up together!—this 1999 outing was surprisingly meh for two charismatic, well, forces of nature like Bullock and Ben Affleck.
The Lake House
We truly wish we could time-travel back to 2006 to file a lawsuit against the creative team behind this unremarkable movie for somehow robbing Bullock and Keanu Reeves of any chemistry they had in Speed and IRL as one our favorite pair of Hollywood best friends!
Two Weeks Notice
With any other leads, this 2002 movie would probably be unforgettable. But pair the buoyant Bullock with the curmudgeon-yet-charming Hugh Grant and you have a will-they-of-course-they-will that we will never not watch when it is on.
Practical Magic
A rom-com with a magical twist? We are in! Bullock has not one, but two relationships worth rooting for in this 1998 movie—dependable Mark Feuerstein as her late husband Michael and dreamy Aidan Quinn as Investigator Gary Halle—but the one we were most invested in was with her wild child witchy sister, played by Nicole Kidman. Who hasn't dreamed of having midnight margaritas with these two?!
Hope Floats
This 1998 Southern charmer about a cheated-on woman returning to her small hometown is special for several reasons: 1. It is the first movie that saw Bullock take on the role of executive producer. 2. Baby Mae Whitman in those adorable glasses as Bullock's daughter and Gena Rowlands as her take-no-shit mother! 3. Helllllo, Harry Connick Jr. Our cup runneth over!
The Lost City
In the vast desert that is modern rom-coms starring, you know, actual stars, The Lost City is a big glass of cool water, filled to the brim with screwball chemistry between Bullock and Channing Tatum, the muscled golden retriever of leading men. Sure, it is ridiculous and over-the-top and easily Bullock's wildest rom-com, but it is also a pleasant way to spend two hours, getting lost with legit A-listers at the top of their game.
Miss Congeniality
OK wait, before you start to practice Gracie Hart's SING demonstration on us, let us justify the decision to not give the 2000 hit—arguably Bullock's most beloved performance—the rom-com crown: Her romance with fellow FBI agent Eric (a totally swoonworthy and suave Benjamin Bratt) is secondary to Gracie's transformation, the beauty pageant investigation and her delicious rapport with Michael Caine. (And we didn't want to have to do this, but we will to make our point: The 2005 sequel revealed their romance fizzled out even quicker than it started. We thought he wanted to date her, love her, marry her!)
The Proposal
Dare we say Bullock has the most chemistry with Ryan Reynolds than any of her other co-stars? Oh, we went there, and we bought property. Just look at their irresistible and banter-filled journey from hate-to-love in this 2009 hit about a demanding boss (Bullock) forcing her young assistant (Reynolds) to marry her in order to avoid deportation to Canada. Turns out, it does take two to make a thing go right! Add in the legendary Betty White (R.I.P) as kooky Grandma Annie and you have comedy gold.
While You Were Sleeping
Bullock's first outing in the rom-com genre also happens to be her strongest, showing off her singular talent for being so damn lovable. No one else could have made the character of Lucy—a lonely train token collector who saves her secret crush's life, only for his family to think she is his fiancée—work in the way Bullock did and she got the Golden Globe nomination to prove it. It was a storyline that could've easily been creepy and taken a turn for a Lifetime thriller, but thanks to Bullock's undeniable charisma and her effortless chemistry with Bill Pullman, While You Were Sleeping is still one of the genre's most beloved offerings more than 25 years after its release. Swoon City, population: Us.