
Continuing from yesterday’s post, today I want to talk about Flip Wilson, a famous American comedian and host of the immensely successful The Flip Wilson Show. It was on this show where Wilson introduced the world to his most famous character, Geraldine.
I have to be honest, I didn’t know who Flip Wilson was until I caught the excellent documentary Why We Laugh: Black Comedians on Black Comedy on TV One. Time Magazine dubbed Wilson “TV’s first black superstar”.
“The devil made me do it”
Flip was a pioneer in many ways and I feel like I missed out on a great comedian. At least we’ve got YouTube now and I can go back and watch some of these old clips, some of which I will embed below.
What I like about Geraldine is that Flip looks good as a woman and the character is funny not because Wilson is in a dress, but because the actual material is very funny.
During the course of his career, Flip also released a couple of comedy albums as the Geraldine chracter, The Devil Made Me Buy This Dress and Don’t Fight The Feeling. From what I could find, they are only available on vinyl and only through third-party sellers as they have long been out of print. However, acquiring these records won’t set you back much.

Many clips from The Flip Wilson Show can easily be found on YouTube and they are also readily available from several retailers, so if you are a big fan and want to add those DVDs to your collection you can consider yourself fortunate.
Flip Wilson is held in high regards in several circles. Unfortunately, he passed away several years ago. However, his legacy will be long-lasting.


{ 5 comments… read them below or add one }
Geraldine was my introduction to the idea of crossdressing. We used to watch the Flip Wilson Show when I was a kid, and I liked to do my own impersonation of Geraldine. Everyone thought it was funny at first, but then my dad told me not to do it anymore.
I agree that Geraldine doesn’t look like a guy in a dress. The material is funny, but part of the humor, at least on the TV show, does come from the subtext of “omg, that’s really a guy!” That’s what everyone is thinking when she pats Ray on the head and says, “Trust me, Ray. Trust me.”
That’s not all there is to her, though. When you listen to his albums, he’s reporting Geraldine’s lines as something someone else said. She’s not a guy in a dress, she’s a woman, and her lines have to be funny without that subtext.
I’m old enough to remember the Flip Wilson Show, but I had forgotten just how funny his Geraldine act was. Thanks for the walk down memory lane!
Melissa XX
I remember his show but not the sketches too well. After going through them again I was impressed with his comic timing and delivery. The writers were at the top of their game and so was Flip. No one like that around today.
I still vaguely remember the Flip Wilson Show as a kid, especially Geraldine! The first time I crossplayed at Otakon, I was dressed as Kagome from the anime series Inuyasha. While I was browsing the dealers room, I heard a man say “Whoa! Geraldine!” as I passed him by. I considered that to be a great compliment and had a fun chat with the guy and posed for a few pics.
I consider watching Flip’s show my initial training in both comedic timing/delivery AND the acceptance of cross dressing in my life. He wears a dress and people like it – why can’t I!