10. Clint Eastwood and Burt Reynolds ("City Heat")
One-time “biggest star on the planet” Burt had taken some blows to his rep after one too many Hal Needham car movies, and sadly, this hyped “tough guys team-up for the ages” with pal Clint only hastened his career downfall. Also, he broke his jaw on the set and got addicted to painkillers. (Cue the opposite of a wheezy Dom DeLuise laugh.)
9. Jennifer Lopez and Ben Affleck ("Gigli")
AKA the movie everyone was fascinated by, but no one actually saw. The Bennifer relationship off-screen captivated a nation for about five minutes. Coincidentally, that's roughly the same amount of time one can stomach this notorious turkey, in which J. Lo infamously and appropriately attempts to instigate oral sex with a not-so-seductive “Gobble gobble.”
8. Warren Beatty and Dustin Hoffman ("Ishtar")
A massive bomb in 1987 whose budget woes became the stuff of legend, "Ishtar" continues to be one of Hollywood’s biggest punchlines, despite the fact that it’s not THAT bad. (Seriously, the "bad on purpose" songs by Paul Williams are uproarious, and Beatty looks like he’s having fun playing against type as a doofus.) Good news for the three people who asked for it: A Blu-ray edition hits in January 2011.
7. Robin Williams and Billy Crystal ("Father's Day")
Maybe it was the shameless, unfunny, apropos-of-nothing guest spot on "Friends" (which aired the night before the flick’s release) that did them in, or maybe both stars had squandered their "City Slickers"/"Jumanji" goodwill (oddly enough, "Good Will Hunting" would resuscitate Williams a few months later). Whichever it was, an hour-and-half of non-stop mugging added up to this Hallmark sentiment: Crappy Father's Day.
6. Brad Pitt and Julia Roberts ("The Mexican")
America did back flips when word got out that the world’s two most attractive megastars were going to make cute and fall in love in a throwback romantic comedy/road movie. But for whatever reason, their characters barely appeared on screen together. Their two brief shared scenes in "Ocean’s Eleven" a few months later proved to be far more charming, as Roberts was able to refrain from guffawing like a trained mule.
5. Mel Gibson and Julia Roberts ("Conspiracy Theory")
Hard to believe there was a time when women wanted to have sex with Mel Gibson, and even harder to believe he could somehow make a conspiracy-spouting nutjob a likable, redeemable dreamboat. But even Mel’s winky face couldn’t make a ridiculously unconvincing love story with Julia and over-the-top Richard Donner action sequences mesh in this all-over-the-map thriller.
4. Al Pacino and Robert De Niro ("Righteous Kill")
What did we want? That awesome diner scene from "Heat" expanded to two hours. What did we get? A run-of-the-mill cop thriller that gave a meaty role to the ugliest member of NKOTB. (We still love ya, Donnie.)
3. George Clooney and Catherine Zeta-Jones ("Intolerable Cruelty")
Two ridiculously attractive leads mixed with the quirky sensibilities of the Coen Bros. should’ve at least made for a fascinating cinematic experiment. What resulted was a run-of-the-mill screwball romantic comedy whose best scenes featured Bruce Campbell and Billy Bob Thornton on a TV screen. At least CZJ was looking smoking hot, which could be considered tolerable cruelty.
2. Kurt Russell and Kevin Costner ("3000 Miles to Graceland")
Few will argue that Russell and Costner were past their prime when they joined forces as casino robbers disguised as Elvis impersonators. (Okay, we take that back…Russell will be in his prime for all eternity, no matter how many clunkers he churns out.) Costner tries way too hard to come off as a Tarantino-esque badass, and the novelty of seeing Russell with a pompadour wears off awfully fast.
1. Jean-Claude Van Damme and Dennis Rodman ("Double Team")
We admit to using the term “megastar” rather loosely in this context, but this strained attempt at a basketball pun effectively ended Van Damme’s status as a theatrical leading man and killed Rodman’s acting career before it even started, as he pretty much acts the same way here as he did on the court (flamboyant but unmemorable).