Sandra Bullock’s Best Comedies, Ranked

If watching the trailer for upcoming comedy The Lost City (starring Sandra Bullock, Channing Tatum, and Daniel Radcliffe) has you aching for a good Sandra Bullock-led laugh, look no further. Just watching that trailer once is enough to make you nostalgic for all her best comedic performances so far. She’s had some truly iconic roles in the films that made our list, and while we left some of her biggest hits like Speed and Practical Magic off because they seemed to fit better into other genres, there are still seven absolutely charming comedies you have plenty of time to check out before The Lost City makes its debut.

7. Miss Congeniality 2: Armed & Fabulous

Of the seven funniest Sandra Bullock comedies, Miss Congeniality 2: Armed and Fabulous is probably the weakest. And it has nothing to do with anything lacking in Sandra’s performance. Trying to duplicate the magic of that first, iconic film was probably a mistake, but there are some genuinely hilarious laughs within this movie’s 1 hour and 55 minute runtime, which makes it worth your while. Especially so if you’re in the mood to watch Gracie save her bestie, Cheryl Frasier, again, or if you’ve recently watched Miss Congeniality and must complete the duet.

6. While You Were Sleeping

What’s a girl to do when she saves a man from an oncoming train, his family mistakenly thinks she’s his fiance, and then she falls in love with his brother? That’s exactly the question Sandra’s character is facing in While You Were Sleeping, a somewhat Christmas-y movie, that plays around with a funny, yet convoluted love story. This one is especially fun if you are looking for a throwback Sandra film or have a special affinity for Bill Pullman or Peter Gallagher. It’s always interesting to watch an actor’s early roles and While You Were Sleeping comes just eight years after Bullock’s first credited work, so it’s early enough to really give you a good idea of where she started.

5. Ocean’s 8

Just as I would classify all the Ocean’s movies heist comedies, Ocean’s 8 definitely delivers on all fronts. The cast is incredible, the action riveting, the comedy, hilarious. The comedy side of things definitely falls heavily on the head of Sandra Bullock, with substantial help from a few of the other experienced comedic actors, including Mindy Kaling, Awkwafina, and Anne Hathaway. There’s just nothing like a good caper to bring out some truly hilarious hijinks, even if you find yourself giggling with glee at the situation more than the written jokes. Let’s face it: it’s hard not to have a smile on your face throughout most of Ocean’s 8.

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4. Miss Congeniality

Back in 2000 we needed the laughs that Gracie Lou Freebush, sorry, Gracie Hart, delivered as she went undercover in the Miss United States pageant to bring down a suspected serial killer. From seeing her physical transformation into a true contender for the title, to watching as she dismantles the expectations of a good contestant (pizza and beer the night before the show?), Sandra Bullock made Miss Congeniality a true classic, and not just as a female-led comedy. The movie is impeccable, with supporting cast members like Michael Caine, Candice Bergen, Benjamin Bratt, Ernie Hudson, William Shatner, and Heather Burns bringing their best to the table, helping to elevate the insanely genius comedic skills Sandra Bullock always delivers.

3. Two Weeks Notice

While Sandra Bullock and Hugh Grant don’t work together often, their pairing in Two Weeks Notice is absolute perfection. Hugh plays his needy, rich, arrogant property developer, George Wade, in the truest of Hugh style. His dry delivery and immaculate timing pair nicely with Sandra’s penchant for brutal honesty and incredible physical comedy. Her character, Lucy Kelson, is the spirited, socially conscious crusader of George’s nightmares. She literally lays down in front of wrecking balls and chains herself to historic landmarks to stop developers in their tracks. Watching these two play characters so diametrically opposed to the other, but also unable to resist the other, is that special magic that only the best rom-coms find. If you haven’t had a chance to watch this duo on screen together, now is the perfect time to do so. They compliment each other so well and it makes for one hell of a great movie.

2. The Proposal

Arguably her best rom-com to date, 2009’s The Proposal with Ryan Reynolds, Betty White, Mary Steenbergen, and Craig T. Nelson is original concept gold. While the print romance genre is chock full of fake dating and fake marriage stories, those adaptations don’t always make it to the big screen. This story showed why those tropes can be incredibly compelling and so much fun to watch. Start with a threat to a valued career, end with two people who accidentally caught feelings along the way and you are on your way to what makes romantic comedies worthy of their own genre. The highway of movies that tried to take their lead characters from enemies to lovers is littered with examples of terrible chemistry, forced storylines, and general awkwardness, but The Proposal runs the gauntlet and comes out the other side with a terrific movie to show for it in the end.

1. The Heat

While not technically a rom-com, and maybe more a buddy comedy, The Heat is some of Bullock’s finest work, bar none. Alongside Melissa McCarthy, we get to see another interpretation of an FBI agent, this time the perfectionist, pain in the ass who lives for the job; the one who makes everyone’s lives miserable because she wants to follow protocol all of the time. That is until she meets a local Boston cop who has no regard for rules as long as she keeps scooping bad guys off the street. The chemistry between these two has us wondering how it’s possible they don’t work together more often. While we don’t need The Heat II, McCarthy and Bullock should definitely find another original comedy project to work together on in the near future. Their interplay is the highlight of the film, dwarfing the storyline, the supporting cast, and even the snappy dialogue. And seriously now, if any movie deserves a sequel, this one could definitely have supported one. There’s enough crime to investigate in Boston that these two could certainly have partnered up to take down another major crime ring or a serial killer or something.

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