Einhorn, "Ace Ventura Pet Detective"
Einhorn, while packing away Mr. Winky, who many moviegoers remember. This crazy woman was responsible for forcing Jim Carey to stick his face into the business end of a plunger and for a group of Miami's finest to simultaneously spit in disgust.. Lois Einhorn is one of the most memorable transgender characters of the last twenty years.
Dil "The Crying Game"
One of the most disturbing movies of all-time, the indy flick "The Crying Game" features a transgender character who ends up showing off her man-junk, shocking audiences all over the world. What makes the transgender character Dil so memorable is that nobody knew she was a he until his/her ying-yang was dangled in the face of an IRA extremist.
Roberta Muldoon "The World According to Garp"
Garp" featured Robin Williams, John Lithgow played the role of Roberta Muldoon, a former NFL tight end who became a transgender female. Lithgow's transgender character was so memorable, he received a nomination for Best Supporting Actor.
Brandon Teena "Boys Don't Cry"
Hilary Swank won an Oscar for Best Female Actor for her role as Brandon Teena, a young transgender female. Based on a true story, "Boys Don't Cry" tells the story of a young Nebraska transgender female who falls in love with a sexy, energetic women she meets in the small town of Falls City. However, it is not Swank's flawless performance that makes Brandon Teena a memorable transgender character; instead it's the hot, lesbian love scene between her and fellow actress, Chloe Sevigny.
Judy "Better than Chocolate"
"Better than Chocolate" is one of those quirky lesbian movies that features a couple hot girl-on-girl scenes. However, the movie has a transgender character who is part of a critical subplot. Judy, a man who really wants to undergo a sex change in order to become a woman, falls in love with a lesbian bookstore owner while befriending the mother of the lesbian lead character.
Dr. Frank-N-Furter "The Rocky Horror Picture Show"
"The Rocky Horror Picture Show" introduced arguably the most popular transgender characters of all-time in the devious Dr. Frank-N-Furter. Dr. Frank-N-Furter's character is etched in mortality as he seduced both male and female characters. He also killed Meatloaf with a pick ax.