Tom Hanks as Kip Wilson/Buffy

Series: Bosom Buddies

Episode(s): Multiple

Tom Hanks has shown amazing range in films, such as "Big," "Forrest Gump," and "Philadelphia," and it all started with this transformative role as one of two pals who must disguise themselves as women to rent an apartment.

David Cross as Tobias Fünke/Mrs. Featherbottom

Series: Arrested Development

Episode(s): Multiple

Tobias takes a positive goal — remaining close to his daughter — coupled with an ill-attempt at his atrocious acting and failed Britishisms — such as "Who wants a banger in the mouth" — and creates a scene for the ages.

Jamie Farr as Maxwell Klinger

Series: M*A*S*H

Episode(s): Multiple

Max Klinger is most remembered for his endearing and repeated attempts to be discharged from the Army for mental instability, which he tried to prove by constantly wearing elaborate women's clothing. As usual, M*A*S*H takes a serious look at the lengths people will go to leave the service AND is still genuinely funny.

Martin Lawrence as Sheneneh Jenkins

Series: Martin

Episode(s): Multiple

Martin Payne's neighbor, Sheneneh, is a sassy, fun, and hilarious woman. The character is simultaneously a send-up of stereotypes and an homage to strong-willed women who own themselves and their image.

Max Baer, Jr. as Jethrine Bodine

Series: The Beverly Hillbillies

Episode(s): Multiple

The show's lovable lug, Jethro Bodine, dressed in women's clothing to play his sister, Jethrine. Besides the comedy, Jethrine's appearance is memorable for two reasons: her voice is dubbed by an actual women (making it all the funnier) and Baer looks pretty darn good as a woman.

Neil Patrick Harris as Barney Stinson

Series: How I Met Your Mother

Episode(s): I Heart NJ

Always the ladies' man, Barney has never shied away from a challenge. Even his biggest challenge of all: getting a lesbian to be interested in him. The show implies he has tried before, and will try again. Lucky for us, the sight of a lipstick-wearing Barney is too good to wish him much success.

John Ritter as Johnette in The Love Boat.

Picture and video clip not currently available

for "Grandma Jack" episode of  Three's Company.

John Ritter as Jack Tripper/Grandma Tripper

Series: Three's Company

Episode(s): Grandma Jack

Tripper was good at playing pretend, just like Ritter himself. From acting like a gay man around their landlord to dressing as his grandmother to win a female-only baking contest, Ritter's go-for-broke comic chops are in full effect.

Bonus Drag Appearance: John Ritter also appeared in drag on The Love Boat in the 1st season.

Gary Anthony Williams as Clarence "Clarice" Bell

Series: Boston Legal

Episode(s): multiple episodes

Clarice, the cross-dressing alter-ego of Clarence Bell, was supposedly fired for requesting maternity leave and told Alan "They don't let me take maternity, they stare at my knockers. Know what I'm sayin'?" Spoken like a truly ticked-off transvestite!

Tracy Morgan as Tracy Jordan

Series: 30 Rock

Episode(s): Believe in the Stars

While attempting to prove that white women have it easier then black men in the US, Tracy ups his speaking by an octave, puts on whiteface, and dresses like a woman. And Lobster hands. Because he ran out of makeup. Yeah, it's ludicrous. And hilarious. Just ask Oprah!

Alexander Skarsgard as Eric

Series: True Blood

Episode(s): Frenzy

A traumatized Lafayette imagines a yelling Lettie Mae Thornton as the vampire who tortured him. Plus, how could we pass up the sight of Alexander Skarsgard in a dress?

Lucille Ball as Lucy Ricardo

Series: I Love Lucy

Episode(s): multiple

Whether she was dressing like a man to sneak into Ricky's shows or as Harpo to do the famous mirror stunt with the real Harpo Marx, Lucy had a knack for finding comedy in these early gender-bending stories.