The complete history of Rain Day hat bettors
- 1939 – Al Abrams, Sportswriter
- 1940 – No Record
- 1941 – Chester Smith, Sportswriter
- 1942 – No Record
- 1943 – No Record
- 1944 – Whitney Martin, Correspondent
- 1945 – Harry Keck, Football Coach
1946 – Jack Dempsey, Boxing Champ
- 1947 – Bing Crosby, Singer/Actor
- 1948 – Bob Hope, Comedian/Actor
1949 – Vince Johnson, Correspondent
1950 – Eddie Clover, Magician
1951 – Captain Roach, Harrisburg
- 1952 – Tex Litman, Restaurateur
1953 – Tex Litman, Restaurateur
1954 – Bill Corum, Midwest Newspaper Reporter
1955 – Bob Prince, Sportscaster
1956 – Dr. William McClellan, Coroner
1957 – Bob Considine, Sportswriter
- 1958 – Major Don Johnston, Air Guard
- 1959 – Karl Ide, TV Newsman
1960 – Three Stooges, Comedians/Actors
- 1961 – Eleanor Shano, Weather Reporter
- 1962 – Eleanor Shano, Weather Reporter
- 1963 – Cassius Clay, Boxing Champ
- 1964 – Arnold Palmer, Golf Pro/Champ
- 1965 – John Charles Daily, TV Moderator
- 1966 – Punxsutawney Phil, Weather Prognosticator
- 1967 – Del Miller, Harness Racer
- 1968 – Linda Richards, TV News Reporter
- 1969 – Paul Long, TV News Reporter
- 1970 – Red Donley, Sports Reporter
- 1971 – Jack Bogut, Disc Jockey
- 1972 – Al Abrams, Sports
- 1973 – Bill Curry, TV Sports Reporter
- 1974 – Jack Fleming, TV Sports Reporter
- 1975 – Bob Kudzma, TV Weatherman
- 1976 – Myron Cope, Sports Reporter
- 1977 – Johnny Carson, Tonight Show Host
- 1978 – Bob Kudzma, TV Weatherman
- 1979 – Lou Brock, Baseball Star
- 1980 – Bill & Patty Burns, TV News
- 1981 – Joe DeNardo, TV Weatherman
1982 – Myron Cope, Sports Reporter
1983 – Tom Kite, Golfer
1984 – Franco Harris, Pittsburgh Steeler
1985 – Willard Scott, NBC Weatherman
- 1986 – Rick Woods, Pittsburgh Steeler
1987 – Harry Anderson, Actor
1988 – Sally Wiggin, WTAE TV Co-anchor & Mario Lemieux, Pittsburgh Penguin
1989 – Dennis Bowman, WPXI Weatherman & Hank Williams Jr. , Country Western Star
Side Bet: Jan Loughman, KDKA Weathermen
1990 – Andy Van Slyke, Pittsburgh Pirate
- 1991 – Sophie Masloff, Mayor of Pittsburgh
- 1992 – City of Niceville, Florida
- 1993 – Mason City, Iowa
- 1994 – Mike Love, Beachboys
- 1995 – Jaromir Jagr, Pittsburgh Penguin
- 1996 – Troy Aikman, Dallas Cowboy
1997 – Fran Drescher, Actress
- 1998 – Jay Leno, Tonight Show Host
- 1999 – B94, FM Radio
- 2000 – Mr. Rogers & Mr. McFeely
- 2001 – Dixie Chicks, Country Singers
- 2002 – Sara Rush & Kent Tekulve, Pittsburgh Pirate
2003 – Chubby Checker, Singer
2004 – Will Ferrell, Comedian/Actor
- 2005 – Donald Trump, former President of the United States
2006 – Troy Polamalu, Pittsburgh Steeler
- 2007 – William Sanderson, Actor
2008 – Luke Ravenstahl, Mayor of Pittsburgh
- 2009 – Miss America Katie Stam
- 2010 – Annise D. Parker, Mayor of Houston Texas
- 2011 – Josh Koscheck, UFC Fighter
2012 – Brett Keisel, Pittsburgh Steelers
- 2013 – Coleman Scott, 2012 Olympic Bronze Medalist
- 2014 – Patricia Heaton, Actress
2015 – Robert Rohanna/Rachel Rohanna
2016 – The Rainmaker of Punxsutawney Phil & the Groundhog Club’s Inner Circle & West Greene Lady Pioneers “WPIAL Champs & PIAA State Runner-ups
- 2017 – Bob Huggins: West Virginia University Men’s Head Basketball coach
2018 – Heather Abraham, KDKA television news personality
2019 – Bob Pompeani, KDKA sports anchor
2020 -Stephen Cropper, WPXI Chief Meteorologist
- 2021 – Josh Reedy, guitar player and background vocalist for country artist Thomas Rhett
2022 – Rick Sebak, WQED producer
- Designates a rain year.




