Past winners of the Punniest of Show portion of the O. Henry Pun-Off.

2010
1st – Justin Golbabi and Kelly Dupeck
2nd – Jacob Dodson
3rd – Judy Dean and June Morris

2009
1st – Kirk Miller
2nd – Andy Balinsky
3rd – Eirik Ott

2008
1st – Carmen Petrick
2nd – Kara Templeton
3rd – Simon Friedlander

2007
1st – Joe Sabia
2nd – Carmen Petrick
3rd – Linda Endridge

2006
1st – Eirik Ott
2nd – Jim Ertner
3rd – Lloyd Dissmore

2005
1st – Francis McGrath
2nd – Jim Hahn
3rd – Patrick Tanzola

2004
1st – Ben Glazer
2nd – Gita Mani and Archana Sinharah
3rd – Laurie Ann Poole

2003
1st – Carlotta “Candy Rapper” Stankiewicz
2nd – Judy Dean and June Morris
3rd – Stephen Nagle

2002
1st – Jim Ertner

2001
1st – Steve Brooks
2nd – Jim Ertner

2000
1st – Tiffany Wimberly

1999
1st – Jim Hahn

1998
1st – Francis McGrath

1997
1st – Steve Brooks

1994
1st – Steve Brooks

1993
1st – Steve Brooks