The 25 Least Attractive Cross-Dressing Men In Movies

Ron Perlman—great actor, ugly woman. The Sons of Anarchy star plays a transsexual named Phyllis in his new comedy 3, 2, 1... Frankie Go Boom, and as you can see in the image above, his gruff Shar Pei features don't translate well to womanhood. He needn't feel bad about it, though, as many square-jawed, stubble-faced actors have looked absolutely heinous in drag. Behold: The 25 Least Attractive Cross-Dressing Men In Movies. Be careful, they may burn your retinas.

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Compiled by Justin Monroe (@40yardsplash)

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25. Adam Sandler as Jill Sadelstein in Jack and Jill (2011)

24. Eddie Murphy as Mama Klump in The Nutty Professor (1996) and Nutty Professor II: The Klumps (2000)

23. Robin Williams as Mrs. Euphegenia Doubtfire in Mrs. Doubtfire (1993)

22. Dustin Hoffman as Dorothy Michaels in Tootsie (1982)

21. Nathan Lane as Albert Goldman in The Birdcage (1996)

20. Brandon T. Jackson as Charmaine Pierce in Big Mommas: Like Father, Like Son (2011)

19. Miguel A. Núñez Jr. as Juwanna Mann in Juwanna Mann (2002)

18. Tony Curtis as Joe and Jack Lemmon as Jerry in Some Like It Hot (1959)

17. Daniel Davis/Ed Wood as Glenda in Glen or Glenda (1953)

16. Harland Williams as Roberta, Michael Rosenbaum as Adina, and Barry Watson as Daisy in Sorority Boys (2002)

15. Johnny Depp as Bon Bon in Before Night Falls (2000)

14. Tyler Perry as Madea in Diary of a Mad Black Woman (2005), Madea's Family Reunion (2006), Meet the Browns (2008), Madea Goes to Jail (2009), I Can Do Bad All by Myself (2009), Madea's Big Happy Family (2011), Madea's Witness Protection (2012)

13. David Spade as Monica in Jack and Jill (2011)

12. Martin Lawrence as Big Momma in Big Momma's House (2000), Big Momma's House 2 (2006), and Big Mommas: Like Father, Like Son (2011)

11. Shawn Wayans as Brittany and Marlon Wayans as Tiffany in White Chicks (2004)

10. Eddie Murphy as Rasputia in Norbit (2007)

9. Johnny Depp as Ed Wood in Ed Wood (1994)

8. Hugo Weaving as Mitzi Del Bra, Guy Pearce as Felicia Jollygoodfellow, and Terence Stamp as Bernadette Bassenger in The Adventures of Priscilla, Queen of the Desert (1994)

7. John Travolta as Edna Turnblad in Hairspray (2007)

6. Gene Hackman as Sen. Kevin Keeley in The Birdcage (1996)

5. Eddie Murphy as Grandma Klump in The Nutty Professor (1996) and Nutty Professor II: The Klumps (2000)

4. Wesley Snipes as Noxeema, Patrick Swayze as Vida, and John Leguizamo as Chi-Chi in To Wong Foo Thanks for Everything, Julie Newmar (1995)

3. Ron Perlman as Phyllis in 3, 2, 1... Frankie Go Boom (2012)

2. Tim Curry as Dr. Frank-N-Furter in The Rocky Horror Picture Show (1975)

1. Divine as Divine/Babs Johnson in Pink Flamingos (1972)