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

2022 (In Person, but in October)
1st – Erika Ettin
2nd – Gabriela Pedroza
3rd – Amanda Hopkins

2021 (Virtual)
1st – Robin Roper
2nd – Katy Stevens
3rd – Martha Louise

2020 (Virtual)
1st – Jonah Spear
2nd – Gabriela Pedroza
3rd – Sarah Bennett

2019
1st – Jerzy Gwiazdowski
2nd – Sam Corbin
3rd – Erica Ettin

2018
1st – Toby Miceli-Gwiazdowski
2nd – Marisa Roper
3rd – Jerzy Gwiazdowski

2017
1st – Southpaw Jones
2nd – Toby Miceli-Gwiazdowski
3rd – Annica Eagle

2016
1st – Jerzy Gwiazdowski
2nd – Southpaw Jones
3rd – Michael Kohl

2015
1st – Ben Ziek
2nd – Southpaw Jones
3rd – Gy Odom

2014
1st – Alex Petri
2nd – Ben Ziek
3rd – Andy Balinsky

2013
1st – Ben Ziek
2nd – Alex Petri
3rd – Brian Alger

2012
1st – Jerzy Gwiazdowski
2nd – Gracie Deegan
3rd – Ben Ziek

2011
1st – Gracie Deegan
2nd – Justin Golbabi and Kelly Dupeck
3rd – Andrew Balinsky

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

1995
1st – Lee Jackson

1994
1st – Steve Brooks

1993
1st – Steve Brooks

1989
1st – Gary Hallock