Stream It Or Skip It: ‘Greg Fitzsimmons: You Know Me’ On YouTube, Finding The Comedian Reflecting Comfortably In His Fifties

Greg Fitzsimmons started his stand-up career at the same time and place as Joe Rogan in early 1990s Boston. Their paths diverged and converged again multiple times since they graduated from the open mics and one-nighters around New England to Hollywood And now Rogan’s new Comedy Mothership In Austin has provided a comfortable home away from home for Fitzsimmons to film his second stand-up special, out now on YouTube.

GREG FITZSIMMONS: YOU KNOW ME: STREAM IT OR SKIP IT?

The Gist: Fitzsimmons has appeared more than 20 times on Rogan’s uber-popular podcast, and more than doubled that number of appearances back on The Howard Stern Show, which resulted in Fitzsimmons getting his own SiriusXM show for more than a decade.

You may recognize him better, though, for his regular panelist appearances in the 2000s on VH1’s Best Week Ever and I Love The… decades series, or on E!’s Chelsea Lately roundtables.

Fitzsimmons also has enjoyed a lengthy career as a comedy writer, working Rogan’s two seasons of The Man Show on Comedy Central, as well as Louis CK’s first sitcom attempt, HBO’s Lucky Louie. But he won his Daytime Emmys for writing on the early years of The Ellen DeGeneres Show. You won’t hear him dishing any dirt on Ellen in this, his second hour (following two half-hours and a 2013 hour for Comedy Central, Life On Stage (now available on Prime Video). Rather, some three-and-a-half decades into performing stand-up, Fitzsimmons finds himself reflecting on how far he has come since sobering up, getting married, and trying to raise his kids to realize how cool he used to be.

What Comedy Specials Will It Remind You Of?: Fitzsimmons came out of the same Boston comedy scene in the late 1980s as his contemporaries Rogan, Louis CK, Bill Burr, Jon Benjamin, David Cross, Nick DiPaolo, and Tom Shillue. While Fitzsimmons may share a lot of common traits or upbringings as those other pale Massholes, his stand-up has kept much closer to the bread-and-butter jokes that keep the laughs going on the comedy club circuit. Not necessarily more adventurous, but by necessity more proven to kill onstage.

Memorable Jokes: If his cap choice didn’t set off any green, white and orange flags for you, then Fitzsimmons’s opening bit certainly fills you in on just how Irish he really is, thanks to his admissions about taking a DNA test.“A little bit is charming. Ninety-nine percent: feels kinda racist.” That leads him into poking holes into any romantic notions you may have about the Irish, playing up their more (or less) colorful stereotypes. At any rate, or at his rate, he’s flipped the script long ago. “I’m sober, married, monogamous, took anger management classes, court ordered, and…” he wants us to know that doesn’t automatically make him a good guy now.

So what kind of a guy is he?

Fitzsimmons actually is happy with where he has landed at age 57, even if he cannot understand why his kids might think their mom is cooler than he is, or if he can only relate to his son through watching sports together on TV, except for the rare time when they witness some “accidental nudity” at the beach in real life.

The Major League Baseball pennant races may be heating up now that October is around the corner, but Fitzsimmons finds no use for baseball in his life or ours, although the recent addition of a clock to speed things up not only proves his point but also gives him an excuse to offer up some additional new rules for the MLB.

Other bits squarely place Fitzsimmons in, if not midlife crisis, then most definitely territory well-trod by men in middle-age. He has jokes about erectile dysfunction, his mixed feelings about getting his prostate checked by the doctor, and his story about attempting to cash the coupon his wife gave him for a shady Thai massage parlor sounds like it could’ve easily been a scene from Curb or Seinfeld. Not that there’s anything wrong with, yada yada, you get it.

Our Take: Plenty of Fitzsimmons’ premises demonstrate why he’s had steady work in writers’ rooms for talk shows and sitcoms alike over the past two decades.

While some set-ups and punchlines feel dated or truly tired (such as when he’s wondering about a pilot’s dreams versus reality, yet pausing to mock the idea of female pilots), those same bits also include interesting observations (such as the late-stage capitalist dread of hearing a pilot have to hawk the airline’s credit card promotions). Similarly, the bit in which Fitzsimmons shares his glee with his son (and in the retelling with us) in seeing a young woman lose her bikini in the Venice Beach surf starts off grossly when he reveals the woman may have actually been a 17-year-old girl, before stopping himself to up her age to 21. A 1990s club comic might not have thought or felt a need to even apologize for perving on a teen, as Seinfeld did in an episode and in real life. Ahem.

Anyhow.

The women in Fitzsimmons’ jokes usually, much like in network sitcoms, have the upper hand or last laugh on him.

And as for how he sees his own life and career, Fitzsimmons is quick to see the brighter side of gratitude for where he’s at. After all, he reminds us that his own dad died at 53, his grandparents in their 40s, and he himself stands at 57, still doing what he loves for a living.

“I’m happy where I am. I’m happy where I’ve gotten in life. because my dream, my dream was never to be a celebrity. That was never in the cards for me. For me, it was about can I get a room full of people to sit down and I can tell jokes and that’s it. And I was able to do that. And I’ve been doing that for 30 years now,” he says. “And I don’t really want any more. I’ve crawled my way to the middle. I’m staying right there! The middle, baby. That’s the sweet spot. That’s where you want to be in life.”

Our Call: STREAM IT. While many of his contemporaries have more fame than he has, they also have become plenty infamous as well, so perhaps he’s in a sweet spot for stand-up in his late 50s, indeed. His brand of stand-up may not surprise you, but it certainly won’t disappoint you, either.

Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.