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With Barbi Benton

Age Difference: 24 years

With Kimberly Conrad

Age Difference: 37 years

With Crystal Harris

Age Difference: 54 years

With Holly Madison

Age Difference: 54 years

Age Difference: 24 years

With Kimberly Conrad

Age Difference: 37 years

With Crystal Harris

Age Difference: 54 years

With Holly Madison

Age Difference: 54 years

Rate:

With Betsy Drake

Age Difference: 19 years

With Dyan Cannon

Age Difference: 33 years

With Barbara Harris

Age Difference: 47 years

Age Difference: 19 years

With Dyan Cannon

Age Difference: 33 years

With Barbara Harris

Age Difference: 47 years

Rate:

With Wendy Neuss

Age Difference: 18 years

With Sunny Ozell

Age Difference: 37 years

With Lisa Dillon

Age Difference: 39 years

Age Difference: 18 years

With Sunny Ozell

Age Difference: 37 years

With Lisa Dillon

Age Difference: 39 years

Rate:

With Mildred Harris

Age Difference: 13 years

He was 29, she was 16.

With Georgia Hale

Age Difference: 16 years

He was 36, she was 19

With Louise Brooks

[no pictures of them together exist]

Age Difference: 17 years

He was 36, she was 19

With Lita Grey

Age Difference: 20

He was 35, she was 15

With Paulette Goddard

Age Difference: 21

He was 43, she was 22.

With Joan Barry

Age Difference: 31

She was 22, he was 53.

With Oona O'Neill

Age Difference: 36 years

He was 54, she was 18.

Their 34 year marriage lasted from 1943 to Chaplin's death in 1977.

Age Difference: 13 years

He was 29, she was 16.

With Georgia Hale

Age Difference: 16 years

He was 36, she was 19

With Louise Brooks

[no pictures of them together exist]

Age Difference: 17 years

He was 36, she was 19

With Lita Grey

Age Difference: 20

He was 35, she was 15

With Paulette Goddard

Age Difference: 21

He was 43, she was 22.

With Joan Barry

Age Difference: 31

She was 22, he was 53.

With Oona O'Neill

Age Difference: 36 years

He was 54, she was 18.

Their 34 year marriage lasted from 1943 to Chaplin's death in 1977.

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With J.D. Salinger

Age Difference: 35 years

He was 53, she was 18.

(No pics of them together, obviously.)

22 year old J.D. Salinger also dated 16 year old Oona O'Neill in the 40s.

Age Difference: 35 years

He was 53, she was 18.

(No pics of them together, obviously.)

22 year old J.D. Salinger also dated 16 year old Oona O'Neill in the 40s.

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(okay, so he's not an actor. ;P )

With Frances Folsom

Age Difference: 28 years

He was 49, she was 21.

With Frances Folsom

Age Difference: 28 years

He was 49, she was 21.

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With Jerry Hall

Age Difference: 13 years

With L'Wren Scott

Age Difference: 23 years

With Luciana Morad

Age Difference: 26 years

Age Difference: 13 years

With L'Wren Scott

Age Difference: 23 years

With Luciana Morad

Age Difference: 26 years

Rate:

With Kristin Davis

(I think this might be a rumor?)

Age Difference: 19 years

With Anne Stringfield

Age Difference: 26 years

(I think this might be a rumor?)

Age Difference: 19 years

With Anne Stringfield

Age Difference: 26 years

BRODO's rating:

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With Karen McDougal

Age Difference: 16 years

With Brooke Burns

Age Difference: 23 years

With Emma Heming

Age Difference: 23 years

With Emily Sandberg

Age Difference: 23 years

With Nadia Bjorlin

Age Difference: 25 years

Age Difference: 16 years

With Brooke Burns

Age Difference: 23 years

With Emma Heming

Age Difference: 23 years

With Emily Sandberg

Age Difference: 23 years

With Nadia Bjorlin

Age Difference: 25 years

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... for better or worse. ;)

Who's cute, and who's creepy?

Who's cute, and who's creepy?

## Added to

53 votes

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list by imanshole

Published 36 minutes, 2 seconds ago
5 comments

76 votes

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list by SwornShadow

Published 3 years, 7 months ago
13 comments

10 votes

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Published 1 year, 10 months ago
1 comment

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4 years, 8 months agoat Mar 12 14:12Btw, True Blood couple:

Stephen Moyer (42) + Anna Paquin (28) = age difference 14 years

4 years, 8 months agoat Apr 4 16:424 years, 8 months agoat Apr 4 18:044 years, 8 months agoat Apr 4 18:274 years, 8 months agoat Apr 4 20:424 years, 8 months agoat Apr 5 1:434 years, 8 months agoat Apr 5 7:024 years, 7 months agoat Apr 6 23:004 years, 4 months agoat Jul 9 21:224 years, 3 months agoat Aug 17 0:584 years, 2 months agoat Sep 23 21:164 years, 1 month agoat Oct 13 2:344 years, 1 month agoat Oct 14 16:064 years agoat Nov 10 10:213 years, 5 months agoat Jun 30 21:123 years, 4 months agoat Jul 18 0:133 years, 3 months agoat Aug 21 10:55n CHARLIE CHAPLIN.... holy crap !!! he was one hell of a pedophile.

2 years, 3 months agoat Aug 15 21:25http://thehairpin.com/2011/12/scandals-of-classic-hollywood-cary-grants-intimate-bromance

2 years, 3 months agoat Aug 15 21:322 years agoat Oct 31 23:211 year, 4 months agoat Jul 15 21:131 year, 4 months agoat Jul 17 15:47