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2024
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Betting $11,000
1364 upvotes
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r/Whatcouldgowrong
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……………..
245 upvotes
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r/NormMacdonald
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Gilbert tries to make Beetlejuice laugh 2005
72 upvotes
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r/ClassicHowardStern
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Montana claims to have the best natural looking fake boobs 1998
NSFW
61 upvotes
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r/ClassicHowardStern
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Michelle Miss Butterface 2004
51 upvotes
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r/ClassicHowardStern
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Win Fred’s Money chance to win $10,000
NSFW
48 upvotes
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r/ClassicHowardStern
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Howard wears OJ t-shirt on Letterman 1994
42 upvotes
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r/ClassicHowardStern
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Montana claims to have the best natural looking fake boobs 1998
NSFW
40 upvotes
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r/howardstern
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Richard and Sal fucking with Gary the Retard
32 upvotes
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r/ClassicHowardStern
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Amy Fisher walks out 2008
NSFW
30 upvotes
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r/ClassicHowardStern
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Betting $11,000
1364
Whatcouldgowrong
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10
9
8
7
6
5
4
3
2
1
0
……………..
245
NormMacdonald
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10
9
8
7
6
5
4
3
2
1
0
Gilbert tries to make Beetlejuice laugh 2005
72
ClassicHowardStern
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10
9
8
7
6
5
4
3
2
1
0
Montana claims to have the best natural looking fake boobs 1998
NSFW
61
ClassicHowardStern
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10
9
8
7
6
5
4
3
2
1
0
Michelle Miss Butterface 2004
51
ClassicHowardStern
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10
9
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6
5
4
3
2
1
0
Win Fred’s Money chance to win $10,000
NSFW
48
ClassicHowardStern
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10
9
8
7
6
5
4
3
2
1
0
Howard wears OJ t-shirt on Letterman 1994
42
ClassicHowardStern
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9
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1
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Montana claims to have the best natural looking fake boobs 1998
NSFW
40
howardstern
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Richard and Sal fucking with Gary the Retard
32
ClassicHowardStern
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7
6
5
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Amy Fisher walks out 2008
NSFW
30
ClassicHowardStern
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