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Major Male Comedy

1996 - Paul Provenza

1997 - Paul Provenza

1996 - Mario Cantone ★ 

1997 - Mario Cantone ★ 

1998 - Mario Cantone ★ 

2000 - Mario Cantone ★ 

1997 - Mal Z. Lawrence

1999 - Lewis Black

2000 - Lewis Black

1996 - Jon Stewart

1999 - Jim David ★ 

2000 - Jim David

1999 - Jeff Ross

2000 - Jeff Ross