41 Regrettably Tacky Photos Of Famous People

Otherwise known as the ’90s.

1. Jennifer Garner

Photographer: “Look, Jen, I know this looks a lot like the SNICK couch but it’s all we could find on short notice. You look great!”

ID: 385303

2. Christina Aguilera

Photographer: “Christina, honey: when I look at you I immediately think Futuristic Indian Princess. Now get in that half of a glass bowl and pretend you’re a kitty-cat.”

ID: 328963

3. Julia Roberts

Photographer: “Julia, you’re gorgeous! The only thing that could make you sexier is a genie costume. Let’s do this.”

ID: 384706

4. Ryan Gosling

Photographer: “Didn’t you see Garden State? It’s cool, trust me. This look made Zach Braff go from a goofy television doctor to a goofy indie actor practically overnight.”

ID: 385266

5. Sharon Stone

Photographer: “A good hat, exposed shoulders, and mom jeans never go out of style… haven’t you ever had Glamour Shots done before?”

ID: 385074

6. Cameron Diaz

Photographer: “Cameron, I want you to spread eagle on top of this stool …but with your knees bent so we can keep it PG-13. But don’t look like you think you look sexy right now, I want your face to look completely blasé. Magnificent!”

ID: 324099

7. Jennifer Connelly

Photographer: “Sorry, Jen. We could only find a leather jacket in the size XXL… but we think you can make it work.”

ID: 347540

8. Tiffiani Amber Theissen

Photographer: “It’s a tasteful nude, out here in this field. But let’s push the envelope just a tad by putting a dandelion in your teeth.”

ID: 361979

9. Eric Bana

Photographer: “Here’s a flower. Do your thing.”

ID: 361822

10. Pink

Photographer: “But the jacket matches your hair! Don’t worry, the pattern is very in right now!”

ID: 384728

11. Celine Dion

Photographer: “Persian rugs are always elegant.”

ID: 384750

12. Angelina Jolie

Photographer: “Trust me, blue eye shadow NEVER goes out of style.”

ID: 384846

13. Sarah Jessica Parker

Photographer: “I’m sorry, but where the fuck did that bottle of Perrier just come from?”

ID: 384808

14. Jessica Simpson

Photographer: “When I heard Jessica Simpson I immediately thought big orange padded room. Do you like it?”

ID: 384734

15. Jennifer Lopez

Photographer: “You’re certainly no angel, Jen. Keep the wings, lose the clothes, and lets slather you up with honey and lube. Can somebody get us some dry ice up in here?”

ID: 361983

16. David Duchovny

Photographer: “Hi, David? I’m the photographer here for the Architectural Digest shoot — is this a bad time? Do you mind getting down from that spherical ball? Okay, um, we can reschedule, you have my card. By the way, GREAT pants.”

ID: 384907

17. Sarah Michelle Gellar

Photographer: “Yes, I want everyone on this shoot shirtless and in overalls. Gay undertones? I don’t see it.”

ID: 385118

18. Natalie Portman

Photographer: “Did you see the shoot I did with Jordan Catalano? Let’s put your hair up and I want you to hold this black plastic tarp. Have fun with it. Great!”

ID: 384799

19. Jennifer Aniston

Photographer: “We’ll put you in homely housewife clothes, it’ll be great!”

ID: 384895

20. Naomi Watts

Photographer: “You’re in a car crash but you’re fine because you’re wearing a helmet that ironically is made from shattered glass. It’s BRILLIANT!”

ID: 384850

21. Melissa Joan Hart

Photographer: “Instead of curling your hair or crimping your hair, let’s do a combination of both — but let’s just do it to certain strands of your hair, not ALL of it.”

ID: 384769

22. Uma Thurman

Photographer: “Did you see that photoshoot I did with Melissa Joan Hart?”

ID: 384879

23. Sandra Bullock

Photographer: “You’re a topless hippie! Oh, I’m sorry about the jeans. All we could find were this pair of JNCO jeans so we tried to make them look a little more dated. It’s fine, nobody’s gonna look anywhere other than your chest, I promise.”

ID: 384787

24. Will Smith

Photographer: “We need more rings.”

ID: 384843

25. Liv Tyler

Photographer: “We don’t have any mirrors here, so Liv, just put the daisies wherever you want and hopefully it works out.”

ID: 384919

26. Heather Graham

Photographer: “I see a retro-futuristic version of Poison Ivy in you. Now lean up against that chain fence and run with it.”

ID: 384760

27. Rose McGowan

Photographer: “Nothing is sexier than a topless girl making a fishface.”

ID: 384963

28. Jake Gyllenhaal

Photographer: “Have you ever heard of Simple Plan? No? Well, we’re going to style you like a Canadian pop punk group anyway.”

ID: 384832

29. Madonna

Photographer: “If you insist on demonstrating your new hobbies, Madge, must it be the one where you swallow and regurgitate your pet goldfish Timmy? All right, then let’s at least have you pose out by the pool…”

ID: 385015

30. Thora Birch

Photographer: “Okay, Thora. I want you to stay still and pretend you’re a blow-up sex doll.”

ID: 385010

31. Kate Beckinsale

Photographer: “The hair, it’s like a bun. But instead of wrapping it completely, let’s spread it all around your head so it looks like there’s a giant spider about to consume her it!”

ID: 385042

32. Anna Paquin

Photographer: “You’ve won a freaking Oscar so I know you can at least pretend that you’re happy so, SMILE!”

ID: 384833

33. Kirsten Dunst

Photographer: “There’s no way you disfigured posing like that, promise.”

ID: 385110

34. Fiona Apple

Photographer: “You’re in the middle of the jungle and you’re terrified. TERRIFIED! You’ll also have perfectly-manicured black fingernails that are nearly two inches long, but it’s for the sake of fashion, so it’ll work.”

ID: 385105

35. Jim Carrey

Photographer: “Hi Jim, here’s a stool.”

ID: 387352

36. Christina Ricci

Photographer: “You’re on Mars, in a space egg.”

ID: 384933

37. Leonardo Dicaprio

Photographer: “Who’s Beavis? I don’t see the resemblance.”

ID: 385054

38. Gillian Anderson

Photographer: “Long black velvet gloves always imply that a woman has class.”

ID: 385070

39. Winona Ryder

Photographer: “I know you’re bummed that you got caught shoplifting, but please just sit over by that fire, drag the flowers into the shot, and pretend like you’re happy.”

ID: 385037

40. Demi Moore

Photographer: “Crimped hair and bows everywhere. Yeah, even the ears.”

ID: 385084

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