The thrill of a great romantic comedy is unlike anything else. From the classic genius of Charlie Chaplin's City Lights, Oscars-sweeping It Happened One Night or perennial audience favorite When Harry Met Sally, it's hilarious and ultimately downright thrilling to witness a seemingly mismatched duo fall head-over-heels.
There's even something to be said for the soothing familiarity of a so-so, formulaic rom-com, the one that's confident in sticking to tropes, never aiming higher than mediocrity, comforting in the same way some find bland, by-the-numbers and inoffensive action or B-movies comforting. Then there's the rom-com that just crashes and burns. According to critics on the Tomatometer, these are the absolute most abysmal attempts at rom-com magic ever.
10. All About Steve (2009) — 6%
The same year that The Hangover obliterated box-office records for R-rated comedy and made him a household name, Bradley Cooper starred opposite Sandra Bullock in this best-forgotten, dour downer about a crossword puzzle creator who becomes obsessed with a cameraman. It's more stalker yarn than chick flick, unpleasant and misguided.
The only reason All About Steve has any kind of a legacy is a classy, gracious move on the part of its star: Bullock showed up in person to accept her Razzie for Worst Actress the same week she won an Academy Award for The Blind Side. Brilliant.
9. Gigli (2003) — 6%
At the zenith of Bennifer 1.0, Ben Affleck and Jennifer Lopez starred in a disastrous crime picture about gangsters and the kidnapping of a prosecutor's brother. To date, this is the final theatrical film of [previously] acclaimed director Martin Brest (Scent of a Woman, Beverly Hills Cop).
Gigli was as much a box-office bomb as it was a cultural punchline for months if not years. The rom-com would-be-caper almost had one high-profile defender. In a marginally negative review, Roger Ebert praised the performances and some of the graphic sex talk.
8. 'Til There Was You (1997) — 5%
Undisputed queens of the rom-com genre (on the big and small screens), Jennifer Aniston and Sarah Jessica Parker both appear in 'Til There Was You... and they're relegated to thankless background roles.
Jeanne Tripplehorn and Dylan McDermott co-star in a wildly derivative, meandering rom-com about a love triangle in an apartment complex. In addition to giving talented stars a backseat, 'Til There Was You makes the cringeworthy mistake of featuring a snippet from Brief Encounter, suffering further from any comparison to one of the great cinematic love stories.
7. Good Luck Chuck (2007) — 5%
A modest box-office hit was lambasted by critics. Dane Cook and Jessica Alba star in a raunchfest about a dentist who meets the girl of his dreams. It aims to be like a Farrelly Brothers movie, sorely missing the heart, or even the humor.
Roger Ebert called Good Luck Chuck "potty-mouthed and brain-damaged" in a scathing review. Esteemed British critic Mark Kermode named it the worst movie of 2007.
6. Material Girls (2006) —4%
Just stick with the Madonna video. Hilary Duff, Haylie Duff and Anjelica Huston star in an oh-so-aughts comedy that went splat with reviewers and audiences.
Material Girls is about cosmetics heiresses who unexpectedly lose their fortune and have to rebuild it from the ground up. Loosely based on Jane Austen's Sense & Sensibility, Clueless this is not. Paper-thin, unsympathetic and materialistic characters are never a big draw with general audiences.
5. A Little Bit of Heaven (2012)— 4%
It's not that a rom-com with terminal illness flat-out can't be done (The Fault in Our Stars and select others have succeeded); it's just, it's probably a bad idea most of the time, unless the script is really great.
The promising but squandered pairing of Kate Hudson and Gael García Bernal tops an equally talented supporting cast including Peter Dinklage, Whoopi Goldberg and Kathy Bates. The grave subject matter isn't handled well at all, though. A Little Bit of Heaven was blasted by critics, and only grossed 1/20th its budget at the box office. Ouch.
4. Playing For Keeps (2012) — 4%
What a smashing cast here: Gerard Butler, Oscar winner Catherine Zeta-Jones, Oscar nominee Uma Thurman, Judy Greer, Dennis Quaid and Jessica Biel.
A great lineup of talent is wasted on a dated, frankly flat-out sexist plot about a children's soccer coach (Butler) who's so hunky he can't help but attract the attention of numerous unhappily married suburban moms.
3. Serving Sara (2002) —4%
Matthew Perry, along with his Friends co-stars, is one of the highest-paid and most famous television stars of all time. Between Serving Sara and the equally maligned The Whole Ten Yards, Perry's potential for a blockbuster film career was cut short.
Serving Sara stars Perry and Elizabeth Hurley in a lowbrow farce about a romance between a divorcée and a process server. Serving Sara wastes its talented cast (including Bruce Campbell and then-star-on-the-rise Amy Adams). A gratuitous scene of Hurley being stripped to her underwear in an airport is pretty much par for the course here.
2. Because I Said So (2007) — 4%
Diane Keaton's singular contribution to the rom-com genre needs no introduction. However, just four short years after the Oscar winner netted another nod opposite Jack Nicholson in Something's Gotta Give, she starred in what may very well be her worst film ever.
Co-starring Mandy Moore, Lauren Graham and Piper Perabo, a rom-com about an overbearing mother and her three daughters received some of 2007's harshest critical notices. Sadly, this was directed by Michael Lehmann, who made the black comedy masterpiece Heathers about two decades prior.
1. Down to You (2000) — 3%
The first and to-date final theatrical film of writer/director Kris Isacsson (a former assistant to Barbra Streisand), Down to You wastes a solid cast including Freddie Prinze Jr., Julia Stiles, Ashton Kutcher, Henry Winkler and Rosario Dawson in schmaltz about college lovers who reignite an old flame.
Critical analysis on Rotten Tomatoes would suggest Down to You is at the bottom of this list not so much because it's wincingly atrocious (certainly not so-bad-it's-good) as it's just utterly hollow, full of good-looking people and scenarios but thoroughly bland as an enterprise.