Angelina Jolie: Cyborg 2 (1993)
Costarring Elias Koteas and Jack Palance
Tagline: ”Future beware: The soul is in the software”
Jolie MAY BE the most famous woman in the world. She’s an Oscar-winning actress, she wakes up next to Brad Pitt, and she benevolently hopscotches around the globe from one crisis zone to the next like Mother Teresa (with better cheekbones). But there was a time when she wasn’t all of this: namely, when she played a robotic terminatrix in a sequel to a Jean-Claude Van Damme film. Cyborg 2 is a rock-’em-sock-’em slice of future schlock in which the 17-year-old Jolie manages to be stiff — even for a cyborg. If you think we’re being harsh, well, even she agrees, telling The New York Times in 2001: ”After I saw it, ? I went home and got sick.”
Most Embarrassing Moment An unfortunate montage cuts back and forth between a topless Jolie getting it on with Koteas and the crying close-up of Palance’s ?leathery face.
Brad Pitt: Cutting Class (1989)
Costarring Donovan Leitch and Jill Schoelen
Tagline: ”Some people would kill to fit in”
In 2001, we asked Brad Pitt which movie he would wipe off his résumé. Without pausing he said, ”I did a teen horror movie. I’ll give you that one. It’s called Cutting Class. Actually, I’ve never seen it.” Well, we have — and it’s atrocious. Not just because Pitt was 25 when he starred in this teen-slasher dud as a horny high school jock who appears unable to dribble a basketball convincingly. And not because it’s a whodunit where you know exactly who did it in the first five minutes. No, it’s mostly because when Pitt winds up with his head clamped in a vise during the film’s climax, the audience knows exactly how he feels.
Most Embarrassing Moment Pitt dresses in one of his girlfriend’s father’s suits and tells her that while her dad is bigger than he is, he’s bigger ”where it really counts.”
Gywneth Paltrow: Hush (1998)
Costarring Jessica Lange and Johnathon Schaech
Tagline: ”Don’t breathe a word”
The same year she? delivered her Oscar-winning performance in Shakespeare in Love, Paltrow popped up in this absurd thriller about a newlywed’s relationship with her possessive horse-breeding mother-in-law (played by Jessica Lange, doing her best Norma Desmond drag-queen impression). Lange’s past-her-prime Kentucky belle is so over-the-top she gnaws on the scenery like chewing tobacco. Unfortunately, all the lost-looking Paltrow can do is look blond and terrified.
Most Embarrassing Moment Lange slips a drug designed to induce premature labor in horses into Paltrow’s dessert.
Ryan Reynolds: Coming Soon (2000)
Costarring Gaby Hoffmann and Spalding Gray
Tagline: ”You’ll want what she’s having”
It must have sounded like a recipe for box office gold:? a raunchy American Pie knockoff, told from the female perspective. Ka-ching! But poor Reynolds looks like he’d rather be anywhere but this movie, in which he plays an Upper East Side trust-fund rebel trying to come across as a sensitive misfit. Sadly, Reynolds’ wispy facial hair gets to show more range than he does — it literally changes shape from scene to scene, going from soul patch to full-on Vandyke. At one point, a swooning female admirer looks at him dreamily and sighs, ”So Emilio Estevez!” This is? meant as a compliment.
Most Embarrassing Moment Reynolds — on stage with his emo band, Oedipus Wreck — dedicates a song called ?”Love a Woman” to the girl he can’t have.
Daniel Craig: A Kid in King Arthur's Court (1995)
Costarring Thomas Ian Nicholas and Kate Winslet
Tagline: ”Joust do it”
Back when Pierce Brosnan began sporting the James Bond tux, Craig paid his dues as the chivalrous Master Kane in this Disney kiddie flick about an awkward 14-year-old Little Leaguer (American Pie‘s Nicholas) who is magically transported back in time to the medieval days of Camelot. Craig plays the film’s Mr. Miyagi mentor character, teaching the nerdy lad from the future about archery and jousting. Come to think of it, he’s not unlike 007’s Q.
Most Embarrassing Moment It’s hard to take Craig seriously as he hits on Winslet’s hot-to-trot Princess Sarah while wearing snug Robin Hood leggings.
Johnny Depp: Private Resort (1985)
Costarring Rob Morrow and Andrew Dice Clay
Tagline: ”Where every room has a great view”
In the wake of Porky’s, the ’80s witnessed a tsunami of raunchy teen sex-romp comedies, which quickly became a who’s who of future Hollywood talent. There was Fast Times at Ridgemont High starring Sean Penn, Risky Business starring Tom Cruise, and — a few rungs down — this roundelay of hot-weather high jinks starring a pre?Jump Street Depp and Northern Exposure‘s Morrow as a pair of horndog buddies let loose at a posh hotel brimming with bikini-clad babes, jewel thieves, and Andrew Dice Clay’s hairy back.
Most Embarrassing Moment On the run from a bad guy, Depp hides out in an aerobics class. Ogling a shapely butt in front of him, he declares, ”I’m in love.”
Eva Longoria: Carlita's Secret (2004)
Costarring Playboy Playmate Alejandra Gutierrez
Tagline: ”Before she was a ‘Desperate Wife’…she had a little secret”
Exiled straight to DVD the same year that she first arrived on Wisteria Lane as a Desperate Housewife (and six years after she was crowned Miss Corpus Christi), this cheapie stars Longoria as a smoldering dancer whose Flashdance dreams are dashed when she’s blamed for a Miami nightclub murder she didn’t commit. Sadly, it’s the only crime Longoria’s not guilty of in this film, which was released shortly after her equally obscure (and dreadful) Señorita Justice.
Most Embarrassing Moment A famous female salsa dancer hits on Longoria by feeding her a maraschino cherry just like the one on her neck tattoo.
Ben Affleck: The Third Wheel (2004)
Costarring Luke Wilson and Denise Richards
Tagline: ”The only thing they didn’t have on their perfect date…was? any privacy”
Don’t always help your friends. That’s the lesson Affleck must have taken from this wafer-thin romantic comedy written by longtime amigo Jay Lacopo. Obviously, Affleck’s up-and-down-and-up-again career has withstood more blows? than this disposable romantic comedy about a first date gone wrong could ever dish out. But it’s an interesting entry on his résumé, as it was one of the first films produced by Affleck and Matt Damon’s post-Good Will Hunting media company. Not surprisingly, it sat on Miramax’s shelf for three years. The good news is, it was finally released in theaters…in Italy.
Most Embarrassing Moment Just when you thought Damon had the good sense to sit this one out, he pops up near the end as Richards’ smarmy ex.
Alec Baldwin: Suburban Girl (2008)
Costarring Sarah Michelle Gellar
Tagline: ”Rewriting her dream in the big city”
No one enjoyed the second coming of Alec Baldwin on 30 Rock more than we did. But few recall just how grim things were before that show became a hit. Take this off-putting adaptation of Melissa Bank’s best-seller, The Girls’ Guide to Hunting and Fishing, which pairs Baldwin’s tweedy publishing playboy with a junior (way junior!) editor played by Gellar. Creaky, bloated, and unfunny (the movie, not Baldwin), Suburban Girl becomes just plain creepy when the leads eventually lock lips and Baldwin looks as if he’s trying to swallow Gellar’s entire head like a boa constrictor.
Most Embarrassing Moment Baldwin and Gellar’s first encounter, where they flirt by swapping saucy quips about Ethan Frome.
Jessica Biel: Powder Blue (2009) '
Costarring Ray Liotta and Patrick Swayze
Tagline: ”Hope is found in the darkest places”
Biel plays a single-mom stripper with a coke habit in this Crash rip-off set in L.A. on the most depressing Christmas Eve ever. If you’re the kind of person who visits websites like Mr. Skin and keeps tabs on movie-star nudity, then you already know about this one, since Biel goes topless and drips candle wax on herself onstage. But her real fans will want to give this one a wide berth. Powder Blue went virtually straight to DVD, although it did get a theatrical release ?in Russia and Kazakhstan.
Most Embarrassing Moment Biel gives her ex-con father (Liotta) a lap dance. We told you it was depressing.
Megan Fox: Holiday in the Sun (2001)
Costarring Mary-Kate Olsen and Ashley Olsen
Tagline: ”Filmed at the Bahamas”
You’ve got to admire Megan Fox’s rise. She came out of nowhere and became a household name just by wearing a skimpy tank top in Transformers. Of course, no one ever truly comes from nowhere. As proof, check out this mind-numbing Bahamas-set Olsen twins romp. Fox plays an eye-rolling rich bitch named Brianna who tries to steal a vacationing Ashley’s man, Jordan. And as we all know, no one steals Ashley’s man! Even at age 15, Fox was confident enough in her sexuality to effectively deliver this line when a teen Romeo approaches her by saying, ”What’s up?” Her response: ”Not my temperature.” Ouch! When EW asked Fox about this film back in 2009, she said, ”I had no idea what I was doing; I’d never taken an acting lesson.” Asked if she’d seen the film recently, she replied, ”Oh, f—, no! I would kill myself.”
Most Embarrassing Moment Fox threatens Ashley: ”I get what I want. And this winter break, I want Jordan.”
George Clooney: Red Surf (1990)
Costarring Doug Savant, Dedee Pfeiffer, and Gene Simmons
Tagline: ”Staying alive is only half the battle”
We’ve always admired Clooney because he’s so up-front about his failures, whether it’s baroque, big-budget trash like Batman & Robin or this limp Point Break precursor, which finds him playing a jet-ski-riding, ponytailed coke dealer who battles barrio homeboys on both surf and turf. ”I’ve done some bad jobs along the way,” he admitted to EW in 1999. ”But you’ve got to do them. The Facts of Lifes, the Baby Talks, the Red Surfs. When you’re starting out, those are big breaks.” (He left out Return of the Killer Tomatoes). And if you’ve ever wanted to see Clooney go head-to-head with KISS frontman Gene Simmons on film, your wish is now granted. An interesting footnote: Clooney’s love interest in the film is Dedee Pfeiffer, real-life sister of his One Fine Day romantic costar, Michelle. Wonder if this ever comes up at the Pfeiffer Thanksgiving table?
Most Embarrassing Moment Savant (Melrose Place) somewhat erotically snorts coke off Clooney’s lap as he’s driving a Jeep in a Guns N’ Roses T-shirt.
Jake Gyllenhaal: Highway (2002)
Costarring Jared Leto and Selma Blair
Tagline: ”It started as a desperate ?escape and became the ?wildest ride of their lives”
Here’s a movie that wanted to be the Bill and Ted‘s of the grunge generation. Released between Gyllenhaal’s emergence as an indie poster boy in? Donnie Darko and his Brokeback Mountain Oscar nod, this angsty flannel-clad road movie pairs a mohawked Leto with a drug-dealing Gyllenhaal as two dim-bulb Gen-X knuckleheads on the run from gangsters. By the end, you’re rooting for the gangsters.
Most Embarrassing Moment Gyllenhaal gets beaten up by frat boys while defending a freak-show attraction named Alligator Boy.
Matthew McConaughey: Surfer, Dude (2008)
Costarring Woody Harrelson and Willie Nelson
Tagline: ”Love and waves, that’s what we need in these dark days”
The title’s curious punctuation aside, this stoner comedy features a so-mellow-he’s-comatose McConaughey as a shirtless, weed-smoking surfer (natch!). The actor’s $6 million passion project was a gnarly wipeout. Dude earned a 0 percent on Rotten Tomatoes (yes, that’s out of a possible 100) and grossed $52,132 in theaters. Talk about a bad hit of weed comma dude.
Most Embarrassing Moment McConaughey plays a didgeridoo naked.
Katherine Heigl: Caffeine (2007)
Costarring Mena Suvari and Breckin Meyer
Tagline: ”There’s always something strange brewing”
”I’ve always wanted to do a British accent,” Heigl says on the DVD extras. Let’s be good sports and start with the positive news here: (1) The Grey’s Anatomy actress’ accent is fine. (2) That’s all we’ve got. Look, we loved Heigl in Knocked Up, but romantic comedies don’t come less romantic (or comedic) than this painful, low-budget, London-set doozy about the wacky sexual shenanigans of the staff of a Central Perk-style coffeehouse. It’s so amateurish it looks like it was shot on the wax paper left over from one of the café’s scones.
Most Embarrassing Moment During an excruciating blind date, Heigl daydreams about a clown in a rainbow wig pleasuring himself.
Christian Bale: Equilibrium (2002)
Costarring Taye Diggs and Emily Watson
Tagline: ”In a future where freedom is outlawed, outlaws will become heroes”
Who doesn’t have a sweet tooth for Bale’s fun postapocalyptic dragon-slaying epic, Reign of Fire? But there’s nothing to savor in this shameless Matrix clone with a pasty-faced Bale standing in for Neo. If this is the future, then the future needs a better director, or at least a tanning booth. The highlight is the film’s ”Gun Kata” sequences, where dudes do ninjalike battle with machine guns — not by firing them, mind you, but by hitting each other with them (which kind ?of defeats the whole point of having a gun in the first place). Explaining his choice to star in both Reign and this flop, the soon-to-be Oscar winner told EW in 2007, ”Um, they were experiments for me. And I hope I make more experiments in the future, but more successful experiments.”
Most Embarrassing Moment Bale defies authority by refusing to take his mandated sense-deadening meds, which awakens his long-buried sense of empathy, which in turn makes him want to save a puppy from being killed.
Leonardo DiCaprio: Don's Plum (2001)
Costarring Tobey Maguire and? Kevin Connolly
Tagline: ”Never say what you think”
After Titanic turned DiCaprio into the King of the World, an ex-pal, director R.D. Robb, surfaced with this grainy black-and-white slice of lost-generation misogyny, in which the baby-faced actor (it was shot pre-Titanic, in 1995) and his posse of twentysomething L.A. pals bully the female characters, calling them ”bitches” and worse. Not surprisingly, this was a movie DiCaprio didn’t want his fans to see, claiming he made it as a favor for his friend and never expected it to play theatrically. After some legal wrangling, a settlement ensured that ?the film would never come to a theater (or DVD store or streaming service) near you. In fact, as part of the agreement ?it can be shown only outside of the U.S. and Canada.
Most Embarrassing Moment DiCaprio, sporting a pair of novelty buckteeth, picks his nose, then eats his booger to get a laugh.
Jennifer Aniston: Leprechaun (1993)
Costarring Warwick Davis
Tagline: ”Her luck just ran out”
Given how bad this jolly green turd is, it’s shocking (yet kind of impressive) that they’ve managed to wring numerous movies out of the Leprechaun franchise to date (including our personal favorite, 2003’s Leprechaum: Back 2 Tha Hood.) Of course, we’ll always have a soft spot for the original, because that’s where we first fell for our favorite Friend. Not that Aniston shares our feelings. When asked by an Irish journalist if she had wanted to apologize to his countrymen for the film, she responded, ”I should have apologized. But didn’t that punish me enough?” She has a point. After all, Aniston was forced to wear mom-jean shorts, high-top aerobics sneakers, and a feigned look of terror (or maybe not so feigned, come to think of it) as she runs from a three-and-a-half-foot-tall homicidal troll.
Most Embarrassing Moment Aniston burns the Leprechaun’s nose with her pickup truck’s cigarette lighter.
Paul Rudd: Gen-Y Cops (2002)
Costarring Maggie Q
Tagline: ”Justice…with an attitude”
Wowza. This must be seen to be believed. Never mind that Rudd, born in 1969, is actually a member of Gen-X. Such technicalities seem unavoidable when you’re playing a peroxide-blond, hair-trigger FBI agent sent to Hong Kong to retrieve a Mighty Morphin Power Rangers-looking robot from a band of badly dubbed slapstick terrorists. Not only does Rudd get to ham it up Jackie Chan-style in an underwater gunfight, he also gets to deliver the following line: ”Keep flappin’, dickhead! You’re the one going to the bamboo Alcatraz!”
Most Embarrassing Moment Rudd barks, ”Roseanne Barr Arnold will be President of the United States before you two punks see the light of day.”
Sandra Bullock: Fire on the Amazon (1993)
Costarring Craig Sheffer
Tagline: ”Fight fire with fire”
A year before Speed turned her into America’s Sweetheart, Bullock starred in this jungle adventure she’d no doubt rather forget. Set in Bolivia’s Amazon basin, the cheapie is full of clichéd dialogue like ”The rain forest is no place for a gringo,” said with straight faces. Bullock plays a fiery fanny-pack-wearing crusader helping the locals battle greedy land developers. But the real reason to check it out is the scene in which Bullock and Sheffer, with tribal stripes painted on their faces, drink a vision-quest potion given to them by the natives and make hungry, groping, raw slo-mo love in a bamboo hut to the strains of exotic pan-flute music. ¡Dios mio!
Most Embarrassing Moment Bullock licks the sweat off Sheffer’s chest as if it were the salty rim of a margarita.
Meg Ryan: My Mom's New Boyfriend (2008)
Costarring Antonio Banderas and Colin Hanks
Tagline: ”His mom is dating his suspect. Let the surveillance begin.”
The When Harry Met Sally… star has appeared in more bad movies than good ones during the past decade (The Women, Serious Moonlight, etc.). But this one stands out for being the most self-aggrandizing. Basically, Ryan dons a fat suit at the outset of the film so that everyone else can later tell her how hot she is when she loses weight and blossoms into a sexually liberated mom on the prowl. It’s like Cougar Town crossed with The Klumps. The direct-to-DVD dud costars Antonio Banderas as a smooth art thief whom the post-makeover Ryan falls for, and Colin Hanks as her FBI-agent son who’s onto the Latin lothario. This time around, we won’t have what she’s having.
Most Embarrassing Moment Ryan, in a latex fat suit, sits on the floor at the airport gorging herself on a bag of Krispy Kremes.
Reese Witherspoon: Overnight Delivery (1998)
Costarring Paul Rudd
Tagline: ”When it comes to true love, can they go the distance?”
We don’t mean to gang up on Rudd. So with this aggressively lame road-trip rom-com, we’ll focus on his costar, future Oscar winner Reese Witherspoon, who plays the least naughty stripper ever. After Rudd sends a letter to his long-distance girlfriend wrongly accused of cheating, he hits the road to retrieve it. Riding shotgun is Witherspoon’s perky exotic dancer (stage name: Ivy von Trapp), who teaches Rudd that love had been in the front seat next to him all along. Asked about the film in 2010, Rudd told EW, ”We weren’t redefining cinema in any way.” That’s putting it mildly.
Most Embarrassing Moment Witherspoon tells Rudd she’s having a hard time staying on her side of the car due to his ”James Dean sexual heat.”
Sylvester Stallone: Eye See You (2002)
Costarring Tom Berenger and Charles Dutton
Tagline: ”Survival is a killer”
Originally titled D-Tox back when it still had hopes of a wide release, this sluggish stockpile of stale serial-killer clichés spent three years in limbo before eking out a blink-and-you’ll-miss-it theatrical run. Sly plays an FBI agent haunted by the murder of his girlfriend with a power drill and is sent to a remote clinic for post-traumatic stress disorder. As a blizzard rolls in, one patient starts offing his fellow inmates, and it’s up to you-know-who to save the day. The punny title refers to the killer’s calling card — in one case he writes the letters ”ICU” inside his victim’s eyelids.
Most Embarrassing Moment Never one to let a double entendre go to waste, Stallone impales the killer on a spike while uttering, ”I see you. You see…this?!”
Gary Oldman: Tiptoes (2004)
Costarring Matthew McConaughey, Kate Beckinsale, and Peter Dinklage
Tagline: ”It’s the little things in life that matter”
Where to begin with this drama about two brothers, one normal size (McConaughey) and the other a dwarf (Oldman)? How about the trailer, which not only trumpets ”When the going gets rough, it’s only the size of your heart that counts” but also boasts Gary Oldman ”in the role of a lifetime!”? Or the fact that that role of a lifetime requires him to kneel to play a Southern-accented little person named Rolfe? Tiptoes undercuts its heavy-handed message by taking every opportunity to fetishize McConaughey’s hairless chest. Folks, we give you the holy grail of awful movies!
Most Embarrassing Moment Oldman walks in on his little-person girlfriend having sex with a Little Richard look-alike played by David Alan Grier.