How Rosie O’Donnell Taught Women to Take Risks

“Golf is not a sport. Golf is men in ugly pants, walking.”

If you were in my presence in Southern Indiana in the early 1990s, you might, incorrectly, attribute this quote to me, due to my constant need to repeat this joke, regardless of the time or place. However, the joke belongs to Rosie O’Donnell, a comedian I’d often watch on VH1’s Stand Up Spotlight. I can’t say why I loved that jokes so much. Surely, golf was not such a big part of my life that I felt it needed to be taken down a peg. Rather, I think my love for the joke was based in my connection to the comedian herself. Even in her early stand-up days, Rosie’s comfort with herself was both startling and comforting; so different from everyone else that it immediately causes a gut check in the viewer: are you being as honest as she is?

I was disappointed to hear Rosie O’Donnell was doing a talk show, because in my mid-90s mind, talk shows meant Ricki Lake and paternity tests. Not that I object to either, but it seemed like a misstep for O’Donnell. However, being that I was a TV addict and it was summer, I tuned into The Rosie O’Donnell Show and I was totally blown away. She was like me. She was pop-culture obsessed, remembered obscure details from TV shows and really loved when people sang in a non-ironic, heartfelt way. I was taken aback: someone else was as dorky as I was and was telling people about it — on television?!

For me, being a comedian is directly related to being a Rosie O’Donnell fan. The hardest thing in comedy is putting yourself out there and risking judgment. I think fear of judgment is a problem for male and female comedians alike, but in my experience as a writer and director a the Upright Citizens Brigade Theatre, I notice women especially shy away from stances that could make someone else uncomfortable. O’Donnell’s fearlessness throughout her career (whether it’s her love for Koosh balls or her stances on the Iraq War) remains an inspiration to me and many other female comedians. As UCB actress and improviser Sarah Claspell says “Rosie has always been a strong, funny comedienne, unapologetic for her anti-gun, pro-gay, charity stuff … I don’t always agree with her and her outspokenness often gets her in trouble, but I think it’s important that she stands up for what she believes in and doesn’t hold back because of sponsors or things like that.” Indeed, Rosie would both show her own Donny & Marie dolls to Donny Osmond himself (who didn’t really get the joke) and confront NRA member Tom Selleck (who didn’t really get the non-joke).

Whether they were uncomfortable, delighted or, in the case of William Shatner, being pushed out of their chair by a footrest gone rogue, the guests on The Rosie O’Donnell Show acted like normal people and dumped their canned PR talk. As UCB writer and actress Ari Scott said, “I liked the casual way she spoke with guests. I had the sense she was a real person.” O’Donnell seemed like our person on the inside, bravely asking Wesley Snipes about pie.

O’Donnell was famously influenced by television, pop music and, most of all, Barbra Streisand, so she was aware of the potential power of her show. She put things on television she felt were important including, of course, Broadway shows. For most of us around the country, this was our only consistent contact with live theatre and it directly influenced a generation. “She staged musicals at 3pm a kid in Virginia didn’t get to see. If I hadn’t seen Thoroughly Modern Millie on her show I wouldn’t own tap shoes,” says Jocelyn Guest, UCB writer and actress.

It saddens me that today O’Donnell might be more associated with her fall-out on The View with co-host Elisabeth Hasselbeck than for her comedy talents, but I also think her legacy is clear in the generation of female comedians she influenced.

Also — it goes without saying — A League of Their Own is the best movie ever made.

Caitlin Tegart is a comedian, writer and director often sighted at the Upright Citizen Brigade Theatre and

How Rosie O’Donnell Taught Women to Take Risks