2009
Renee Flaming — Miss Fire Island
Logan Hardcore — Entertainer of the Year

2008
Coco Love — Miss Fire Island
Shi-Queeta-Li — Entertainer of the Year

2007
Stephanie Stone — Miss Fire Island
Sugga Pie Kokko — Entertainer of the Year

2006
Epiphany — Miss Fire Island
Victoria Michaels — Entertainer of the Year

2005
Ginger Moore — Miss Fire Island
Gusty Winds — Entertainer of the Year
The Mariachi Girls — Best Duo/Group

2004
Dakota Sue — Miss Fire Island
Freda Chews — Entertainer of the Year
Twisted Sisters — Best Duo/Group

2003
Nikki Starr — Miss Fire Island
Porsche — Entertainer of the Year
The Rubi Girls — Best Duo/Group

2002
Ariel Sinclair — Miss Fire Island
Mirkala Crystal — Entertainer of the Year
Milan vs. Leila — Best Duo/Group

2001
Kimberly Turner — Miss Fire Island
Delilah Dagger — Entertainer of the Year
The Homecoming Queens — Best Duo/Group

2000 — Coral Anniversary
Viva Sexx — Miss Fire Island
Ariel Sinclair “Gladys Finkelstein” — Entertainer of the Year
Angela Mercy & Freeta Chews — Best Duo/Group

1999
Victoria Weston — Miss Fire Island
Hollie Roberts — Entertainer of the Year

1998
Vanessa Diamond — Miss Fire Island
Delilah Dagger — Entertainer of the Year

1997
Jenna Jaret — Miss Fire Island
Julie — Entertainer of the Year

1996
Gianna — Miss Fire Island
Victoria Weston — Entertainer of the Year

1995 — Pearl Anniversary
Vanessa — Miss Fire Island
Ariel Sinclair — Entertainer of the Year

1994
Trixia Gomez — Miss Fire Island
Peter Taylor “Cher” — Entertainer of the Year

1993
Christina Hemingway — Miss Fire Island
Miss Bitch — Entertainer of the Year

1992
Frenchie — Miss Fire Island
Stefán “Marilyn Monroe” — Entertainer of the Year

1991
Zania — Miss Fire Island
Kevin Baxter “Barbra Streisand” — Entertainer of the Year

1990 — Silver Anniversary
Philomena — Miss Fire Island
Kaleb Stone “Judy Garland” — Entertainer of the Year

1989
Coco — Miss Fire Island
Bobby Herr — Entertainer of the Year

1988
Rochelle Banks — Miss Fire Island
Arian “Leggs” West — Entertainer of the Year

1987
Exotica — Miss Fire Island
Jesse Volt — Entertainer of the Year

1986
Champagne — Miss Fire Island
Codie “Cyndi Lauper” — Entertainer of the Year

1985 — China Anniversary
Vivian Drake — Miss Fire Island
Electra St. Jill — Entertainer of the Year

1984
Nikki Starr — Miss Fire Island
Jesse Volt — Entertainer of the Year

1983
Bill Mead — Miss Fire Island
Chaka Savalis — Entertainer of the Year

1982
Douglas Bennett — Miss Fire Island

1980 — Crystal Anniversary
Dana Manchester — Miss Fire Island

1968
Rita George — Miss Fire Island

1967
Charity — Miss Fire Island

1966
Matty — Miss Fire Island