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Diary of a CEO · 2025-06-02 · 1h 39m

Jimmy Fallon: I Didn't Expect It To Be This Brutal! The Hate Was Something I Wasn’t Prepared For!

Jimmy Fallon traces his obsessive climb from broke LA comic to SNL and The Tonight Show, and the grief, hate, and people-pleasing behind it.

Jimmy Fallon: I Didn't Expect It To Be This Brutal! The Hate Was Something I Wasn’t Prepared For!
The guest

Jimmy Fallon — American comedian and host of NBC's The Tonight Show, formerly a cast member on Saturday Night Live and host of Late Night. Known for celebrity impressions, viral comedy bits, and a vast entertainment business portfolio.

The gist

Jimmy Fallon tells Steven Bartlett the story of his single-minded, childhood obsession with making it onto Saturday Night Live and how he willed it into reality despite years of rejection, near-poverty, and depression in Los Angeles. He recounts his strict Catholic upbringing, his relationship with his late mother Gloria who was his biggest fan and audience, and the emotional weight of losing her. The conversation explores the brutal side of fame, online hate, and the tension between being a relentless people-pleaser and accepting that not everyone will like you. Fallon also reflects on longevity and health after turning 50, fatherhood, and his belief that entertainment will always endure.

Big reveals

  • Reveals he wrote that he would kill himself if he didn't make SNL by 25, and says he meant it at the time.
  • Admits he became an alcoholic at 16, drinking alone while obsessively studying SNL tapes.
  • Calls his broke, friendless years in LA his lowest point, when he broke down mentally and wrote a despairing letter to his best friend.
  • Describes the audition where his Adam Sandler impression finally made Lorne Michaels laugh and won him SNL.
  • Speaks emotionally about his mother Gloria's 2017 death, calling it the toughest thing he's been through.
  • Tells how he wrote and pulled off the famous Mick Jagger mirror sketch in a single day.
  • Says he wasn't prepared for the rejection, cut sketches and haters that came with success.

Things worth remembering

  • In eighth grade he was voted most likely to replace David Letterman on Late Night, which he literally went on to do.
  • Says he never cared about money and would tell his mom to keep the $5 she found in his jeans.
  • His first Saturday-night gig at the Improv required him to follow a surprise set by Jerry Seinfeld.
  • His entire early stand-up act revolved around a troll doll doing celebrity impressions.
  • He negotiated a never-before-granted contract clause letting him quit a sitcom if SNL ever called.
  • Notes Fallon has around 100 million followers across YouTube, Twitter and Instagram.
  • He has his own Universal Studios roller coaster and color-changing Gobstopper sneakers.
  • On an edibles-tinged closing question, he muses that reality might be a simulation someone wandered away from.

Recommended in this episode

Books, products and media the guest or host genuinely endorsed here — with the buy link.

Affiliate link — we may earn a commission at no extra cost to you.

Guest’s ownProduct

Tonight Dough (Ben & Jerry's ice cream)

Ben & Jerry's / Jimmy Fallon

“but you got the ice cream, the Tonight D. Tonight dough ice cream. We've raised a lot of money for uh Serious Fun, which is a great charity.” — Steven Bartlett 01:29:53
Find it on Amazon
Guest’s ownProduct

Gobstopper Skate Shoes

Jimmy Fallon

“Gobstoppers were a sneaker that um we came up with that the more you wear them, the more the leather wears down and they become different colors.” — Jimmy Fallon 01:30:25
Find it on Amazon
Guest’s ownMedia

Holiday Seasoning

Jimmy Fallon

“You made a comedy a series of comedy albums. The last one was called Holiday Seasoning, which I I it's a it's a Christmas album” — Jimmy Fallon 01:29:22
Find it on Amazon
Guest’s ownBook

Your Baby's First Word Will Be DADA

Jimmy Fallon

“data was the first one that was a big deal. It's really the same word on every page. It's just getting your kid to say dada.” — Jimmy Fallon 01:14:43
Find it on Amazon
Guest’s ownBook

Your Baby's First Word Will Be MAMA

Jimmy Fallon

“But then you released Mama. I had to because my wife and and all my female fans were like, Really? You have two daughters” — Jimmy Fallon 01:15:14
Find it on Amazon