100 Sexiest Celebrity Side Shots

by: AnthonyP On  Monday, June 4, 2012

Today we pay tribute to an often underrated section of the female anatomy: the side boob. Women who would never even consider going topless seem to have no problem showing us a view from the side, and for that reason alone we are eternally grateful. And to show our gratitude, we’ve compiled this list of our 100 favorite celebrity side boob pics. Keep in mind, we only accepted entries from the outer side of the breast. After all, the inner side  is nothing more than regular cleavage, and side boob is a different beast altogether.

Enjoy. And let us know who we missed in the comment section.

100. Marilyn Monroe

Screen legend Marilyn Monroe was not above a little sideboob.

99. Jennifer Connelly

Actress Jennider Connelly has fun with a mirror..

98. Daniella Sarahyba

Brazilian model Daniella Sarahyba gives a peak.

97. Faye Reagan

Porn star Faye Reagan gives us some ginger sideboob.

96. Jennifer Aniston

I’d like to make “Friends” with Jennifer Aniston’s sideboob.

95. Jennifer Lawrence

Insert your own “Hunger Games” joke about side boob here.

94. Lake Bell

“Children’s Hospital” star Lake Bell.

93. Erin Wasson

Erin Wasson serves up a kiss with a side of boob.

92. Beyonce

Beyonce’s side boob looks good, even when blurry.

91. Jennifer Lopez

Marc Anthony got bored looking at this side boob.

90. Bree Olson

Charlie Sheen has probably done coke off of the this.

89. Kaley Cuoco

Kaley Cuoco of “The Big Bang Theory.”

88. Cameron Diaz

There’s something about side boob.

87. Aubrey O'Day

With side boob like that, you’ll forget all about her stupid name.

86. Jessica Simpson

Enjoy this pic, because I’m sure Jessica Simpson’s new baby has ruined that side boob.

85. Marley Shelton

Marley Shelton did not write Frankenstein, FYI.

84. Katherine Heigl

Who knew Katherine Heiglwas hiding that much side boob?

83. Alison Brie

Annie’s Sideboob.

82. Glori Santiago

Glory and praise to Gloria Santiago.

81. Halle Berry

Mental note: Watch Monster’s Ball again.

80. Jenna Jameson

Porn star Jenna Jameson.

79. Petra Nemcova

Czech model Petra Nemcova

78. Heidi Montag

This is possibly the worst entry on this list.

77. Heidi Klum

Old-school Heidi Klum side boob.

76. Anne Hathaway

Catwoman sideboob.

75. Ali Landry

Ali Landry: a.k.a. the Doritos Girl.

74. Lea Michele

Glee star Lea Michele.

73. Elisha Cuthbert

Happy Endings star Elisha Cuthbert.

72. Jessica White

Model Jessica White shows some side boob while wearing a stupid hat.

71. Eliza Dushku

Actress Eliza Dushku

70. Tyra Banks

It’s almost enough to make you forget about her awful talkshow.

69. Minka Kelly

With a name like Minka, you know she’s going to be hot.

68. Rihanna

I was going to make an “I’d hit that” joke, but my editor said no.

67. Jamie Chung

Jamie Chung is the best thing to come out of “The Real World.”

66. Vida Guerra

Viva Vida Guerra’s side boob.

65. Tiffani Amber Thiessen

This almost makes up for “Saved by the Bell.”

64. Hilary Rhoda

Sports Illustrated model Hilary Rhoda.

63. Cheryl Cole

British Popstar Cheryl Cole.

62. Denise Richards

Side Boob: It’s Complicated.

61. Candace Rae

Model, actress and side boob promoter Candace Rae.

60. Ana Beatriz Barros

Brazilian hottie Ana Beatriz Barros.

59. Anneliese Van Der Pol

I have no idea who this is, and I don’t care.

58. Dania Ramirez

Dominican TV and film actress Dania Ramirez.

57. Micaela Schaefer

Micaela Schaefer is only known for side boob, and nothing else.

56. Eliza Doolittle

British singer–songwriter-sideboob-shower Eliza-Doolittle

55. Keri Hilson

Another singer, another side boob.

54. Rachel McAdams

Actress Rachel McAdams shows some side boob at the Morning Glory premiere.

53. Mariah Carey

You might not respect her music, but at least respect her side boob.

52. Jennifer Ellison

God bless Jennifer Ellison

51. Tricia Helfer

Cylon side boob.

50. Zoe Kravitz

Way yo go, Lenny.

49. Anna Faris

Probably the funniest side boob on the list.

48. Emmanuelle Chriqui

Emmanuelle Chriqui is Canadian. Also, side boob.

47. Anna Torv

“Fringe” star Anna Torv.

46. Nicole Scherzinger

Nice hat. Just kidding. It’s awful. But who cares.

45. Annalynne McCord

Has that side boob had a “Nip/Tuck”?

44. Lindsay Lohan

Exploited former child-star side boob is my favorite kind of side boob.

43. Marisa Miller

Why is she showing that much side boob in an old elevator?

42. Miley Cyrus

Billy-Ray must be proud.

41. Victoria Silvstedt

And now for some Swedish side boob.

40. Paris Hilton

I wish that was a real bear, and it was mauling her.

39. Kim Kardashian

I know there’s no bear in this picture, but I wish the one from Paris Hilton’s entry was mauling her, too.

38. Megan Fox

That stupid tattoo really brings out your side boob.

37. Gabriela Vergara

She really likes tea… a lot.

36. Britney Spears

Britney Spears in happier times.

35. Olivia Munn

Here’s some side boob that pretends to like video games and sci fi.

34. Jessica Alba

33. Ashley Greene

The only good thing to come out of Twilight.

32. Eva Longoria

“Desperate Housewives” star Eva Longoria.

31. Milla Jovovich

30. Audrina Patridge

If only there was a way to make a joke about “The Hills” and boobs at the same time. Ah, well.

29. Jessica Biel

Jessica Biel shows some side boob at the Oscars.

28. Emily Blunt

I’ll be Blunt. Nice side boob.

27. Eva Mendes

Actress Eva Mendes comes in at number 28.

26. Gisele Bundchen

The side boob that cursed the patriots.

25. Adriana Lima

Victoria’s Secret model Adriana Lima.

24. Sophie Reade

God save the Queen.

23. Miranda Kerr

Another Victoria’s Secret alum.

22. Natalie Portman

She’s come a long way since The Professional.

21. Oliva Wilde

My new favorite actress, at least until the next entry.

20. Angelina Jolie

The side boob that ruined Jennifer Aniston’s marriage.

19. Kate Beckinsale

Actress Kate Beckinsale likes to rub against walls.

18. Rosie Huntington-Whiteley

Transformers 3 star Rosie Huntington Whiteley.

17. Sophie Monk

Some more British side boob.

16. Scarlett Johansson

Some side boob from The Black Widow.

15. Joanna Krupa & 14. Marta-Krupa

Side boob sisters.

13. Katy Perry

Awful songs; nice side boob.

12. Kelly Brook

I’d smile too if I looked that hot.

11. Salma Hayek

Salma Hayek representing.

10. Vikki Blows & 9. Vicky Lloyd

Vikki on Vicky action.

8. Brooklyn Decker

Brooklyn Decker sports some bikini sideboob.

7. Sofia Vergara

“Modern Family ” star Sofia Vergara.

6. Lucy Pinder

Lucy Pinder hops in to number 6.

5. Brook Burke

Brook burke comes in at number 5.

4. Bar Refaeli

Bar Refaeli came close to the top spot.

3. Denise Milani

Too big to fail.

2. Keeley Hazell

Keeley Hazell came up just short.

1. Kate Upton

And the winner is… Kate Upton!