Why Jessi Klein Gave Up the Stand-Up Stage to Make the ‘Funniest’ Comedians Shine

One of the most influential comedy voices of her generation, Jessi Klein spent years working as a development executive at Comedy Central before making the leap to stand-up, SNL, and then head writer for Inside Amy Schumer. Now, in addition to her long-running role as the angsty tween Jessi on Big Mouth, Klein has taken on the role of showrunner for I Love That for You, a new Showtime series co-created by and starring fellow SNL alum Vanessa Bayer.

In this episode of The Last Laugh podcast, Klein opens up about her unconventional road to comedy success and why SNL wasn’t the best environment for her. She also talks about her new book of essays on midlife and motherhood, and tells hilarious stories about working with Amy Schumer, Maya Rudolph, Molly Shannon, and more.

“This has been such a truly special experience, just because the people involved are just so brilliant,” Klein says of I Love That for You, which premiered on Showtime last month. In the show’s pilot, Bayer’s character pretends her childhood leukemia has returned in a bid to win the sympathies of her boss and keep her job. In the process, she tests the sympathies of viewers and enters the age-old debate of what it means for women to be “likable” on TV.

“I can’t wait for the day that likability is not something we really need to get into pretzels over, especially talking about female protagonists,” Klein says. “Ever heard of a little show called The Sopranos? Or Breaking Bad? Even Larry David on Curb Your Enthusiasm. We’re going to like them because we’re going to enjoy this show and these are amazing performers. And Vanessa is likable no matter what she does.”

The first time she saw Bayer perform on “Weekend Update” as her precocious child actress character, Klein thought to herself, “This is one of the funniest people I’ve ever seen.”

And Klein has spent her career working closely with some very funny people. She first made the jump from working behind the scenes at Comedy Central to trying stand-up herself in the mid-2000s and immediately found herself sharing alt-comedy stages with the likes of Nick Kroll, Ali Wong, and Zach Galifianakis. “I can’t believe I was on the same shows as these people,” she says now.

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“I don’t think I ever really imagined I was someone who would really be committed to doing stand-up,” Klein adds. “I loved doing stand-up and it was such a formative part of my creative experience, but the full-tilt, in-your-molecules necessity to be so in it, on the road and out every night, I just didn’t have it in me. I just never committed to it as deeply as you needed to.”

Instead, Klein turned her attention to comedy writing, starting with a job on one of David Spade’s many short-lived talk shows before landing what should have been her “dream job” at Saturday Night Live in 2009.

“I’m so glad I did it, but I really wasn’t very good at it,” Klein says of her one season at the show. “I mean, I really kind of tanked every week. I’m not emotionally cut out for it.

“At the end of the season, if there’s a pass-fail grade, I think I probably was a ‘pass,’” she adds. “Or so I like to tell myself. But if Seth Meyers or anybody’s listening and knows that I was a ‘fail,’ don’t tell me.”

Klein contrasts the competitive atmosphere at SNL with the collaborative environment at Inside Amy Schumer, which she helped launch as head writer in 2013—and for which she won an Emmy Award two years later, beating SNL’s historic 40th season. “I was so into this idea that everyone can just bring the most half-baked idea to the table and we’ll just kind of all do it together to find the idea,” she says.

The seeds of Inside Amy Schumer can be seen in one of the few sketches that Klein did manage to get on SNL: an absurdist commercial parody for Duncan Hines’ new life-sized “Brownie Husband” starring Tina Fey. So it’s fitting that Fey was also there for what was arguably the show’s most iconic moment, or as Schumer once called it, “the best day of my life.”

“Last Fuckable Day” is a sketch that took so long to become a reality that Klein was single when she first came up with the idea and six months pregnant with her son by the time they ended up shooting it.

Klein reveals that when they first started throwing out ideas for actresses to appear in the sketch, which attempts to pinpoint the exact moment that women stop being viewed as sexual objects by Hollywood, she and Schumer imagined it starring women in their sixties and seventies. But they quickly realized the sketch would be funnier—and, sadly, more accurate—if they went younger.

In addition to Fey, they managed to convince Julia Louis-Dreyfus and Patricia Arquette to come on board and play themselves. “That was a real achievement,” Klein says now, reminiscing about the fact that for the first time, the show had actual trailers and a burrito station at craft services because of the A-list talent on hand.

After a long six-year hiatus, Inside Amy Schumer is finally expected to return later this year with five standalone specials on Paramount+. But Klein’s work on I Love That for You meant she wasn’t able to run the writers’ room this time around.

“I just desperately wish I could have worked on it, but I can’t wait to see it,” she tells me. She was just too busy helping the next big female comedy star achieve her wildest dreams.

Listen to the episode now and subscribe to ‘The Last Laugh’ on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.

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