In honor of Adam Sandler dressing in drag for his role in Jack and Jill in theaters this Friday, we thought this week’s Top 5 Tuesday would be in honor of our favorite comedic cross dressing roles. For this list, we decided to stick with roles that featured comedians trying to pretend they are someone of the opposite sex for various reasons. These are not people that are supposed to actually be someone of the opposite sex (ie. Tyler Perry in any Madea movie). Take a look at our list and then let us know what your favorite cross dressing comedian is.


November 9, 2011