TV Head over Heels - Season 1 Episode 10 : Drag Guy Head over Heels - Season 1 Episode 10 : Drag Guy 8/10 by 1 users Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over Heels", a South Beach, Florida video dating service founded by their mother. The staff at Head over Heels includes Ian who produces each client's video, and Valentina the receptionist. Details Casts Posters Images Title Head over Heels - Season 1 Episode 10 : Drag Guy Alternative Titles First Air Date 1997-08-26 Last Air Date 1997-10-28 Number of Episodes 10 Number of Seasons 1 Genres Comedy, Networks UPN, Casts Mitchell Whitfield, Patrick Bristow, Eva LaRue, Cindy Ambuehl, Peter Dobson, Kevin Farley, Heidi Mark, Morgan Fairchild Plot Keywords , Mitchell Whitfield Patrick Bristow Eva LaRue Cindy Ambuehl Peter Dobson Kevin Farley Heidi Mark Mona DuBois Morgan Fairchild Episodes List Head over Heels Season 1 :Episode 1 One Down One Down 1997-08-26 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 2 Gigolo Guy Gigolo Guy 1997-09-02 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 3 Game Show Guy Game Show Guy 1997-09-09 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 4 Vice Guy Vice Guy 1997-09-16 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 5 Witness Guy Witness Guy 1997-09-23 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 6 Hot Guy Hot Guy 1997-09-30 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 7 Spider Guy Spider Guy 1997-10-14 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 8 Reunion Guy Reunion Guy 1997-10-28 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 9 Pilot Pilot 1970-01-01 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over... Head over Heels Season 1 :Episode 10 Drag Guy Drag Guy 1970-01-01 Head over Heels is a 1997 TV series, that aired briefly on UPN. Jack and Warren Baldwin are two brothers who take over the operation of "Head over...