Jack Nicholson

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Jack's back! Never mind how creepy it was how these two wound up together (he dated her daughter — ew!) when serial bachelor Harry (Nicholson) and uptight Erica (Keaton) hooked up it was so good they both burst into tears during post-coital bliss.

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Photo: Columbia

Tags: Jack Nicholson

2 of 68

Jack's back! Never mind how creepy it was how these two wound up together (he dated her daughter — ew!) when serial bachelor Harry (Nicholson) and uptight Erica (Keaton) hooked up it was so good they both burst into tears during post-coital bliss.

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Photo: Columbia

Tags: Jack Nicholson

3 of 68

Jack's back! Never mind how creepy it was how these two wound up together (he dated her daughter — ew!) when serial bachelor Harry (Nicholson) and uptight Erica (Keaton) hooked up it was so good they both burst into tears during post-coital bliss.

0 Comments

Photo: Columbia

Tags: Jack Nicholson

4 of 68

Jack's back! Never mind how creepy it was how these two wound up together (he dated her daughter — ew!) when serial bachelor Harry (Nicholson) and uptight Erica (Keaton) hooked up it was so good they both burst into tears during post-coital bliss.

0 Comments

Photo: Columbia

Tags: Jack Nicholson

5 of 68

Jack's back! Never mind how creepy it was how these two wound up together (he dated her daughter — ew!) when serial bachelor Harry (Nicholson) and uptight Erica (Keaton) hooked up it was so good they both burst into tears during post-coital bliss.

0 Comments

Photo: Columbia

Tags: Jack Nicholson

6 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

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Photo: New Line Cinema

Tags: Jack Nicholson

7 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

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Photo: New Line Cinema

Tags: Jack Nicholson

8 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

0 Comments

Photo: New Line Cinema

Tags: Jack Nicholson

9 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

0 Comments

Photo: New Line Cinema

Tags: Jack Nicholson

10 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

0 Comments

Photo: New Line Cinema

Tags: Jack Nicholson

11 of 68

Making for one of the most talked-about nude scenes in movie history, Kathy Bates dared to go bare in front of Jack Nicholson in the dramedy 'About Schmidt'. So what if they didn't exactly put the hot in hot tub, you've gotta give her major credit for being so damn fearless at any age.

0 Comments

Photo: New Line Cinema

Tags: Jack Nicholson

12 of 68

While charming, retired astronaut Garrett (Nicholson, who makes a few more appearances on this list) may have had his eye on younger women, they were no match for his brassy, tough-as-nails neighbor Aurora (MacLaine) in 'Terms of Endearment'. They may have been closer in age to his usual conquests, but the couple couldn't have been more different. Probably why they made for such a wonderful, sexy pair.

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Photo: Paramount Pictures

Tags: Jack Nicholson

13 of 68

While charming, retired astronaut Garrett (Nicholson, who makes a few more appearances on this list) may have had his eye on younger women, they were no match for his brassy, tough-as-nails neighbor Aurora (MacLaine) in 'Terms of Endearment'. They may have been closer in age to his usual conquests, but the couple couldn't have been more different. Probably why they made for such a wonderful, sexy pair.

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Photo: Paramount Pictures

Tags: Jack Nicholson

14 of 68

While charming, retired astronaut Garrett (Nicholson, who makes a few more appearances on this list) may have had his eye on younger women, they were no match for his brassy, tough-as-nails neighbor Aurora (MacLaine) in 'Terms of Endearment'. They may have been closer in age to his usual conquests, but the couple couldn't have been more different. Probably why they made for such a wonderful, sexy pair.

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Photo: Paramount Pictures

Tags: Jack Nicholson

15 of 68

While charming, retired astronaut Garrett (Nicholson, who makes a few more appearances on this list) may have had his eye on younger women, they were no match for his brassy, tough-as-nails neighbor Aurora (MacLaine) in 'Terms of Endearment'. They may have been closer in age to his usual conquests, but the couple couldn't have been more different. Probably why they made for such a wonderful, sexy pair.

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Photo: Paramount Pictures

Tags: Jack Nicholson

16 of 68

Jack Nicholson and Paul Rudd star in Columbia Pictures "How Do You Know"

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Photo: Hollywood.com Staff/Syndicated by: Columbia Pictures

Tags: Jack Nicholson

17 of 68

Jack Nicholson and Paul Rudd star in Columbia Pictures "How Do You Know"

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Photo: Hollywood.com Staff/Syndicated by: Columbia Pictures

Tags: Jack Nicholson

18 of 68