29. Sebastian Maniscalco: “I Don’t Think That’s Bestiality”
Maniscalco opens up by saying “when you see the world the world sees you,” and lately a whole lot of eyes have been on him. He’s a comedian that takes precious care of every little detail. Even the little spoons he uses at dinner parties have a purpose.
28. Fred Armisen: “I Wasn’t Told About This”
In the episode, Jerry travels to Armisen’s natural habitat of Portland and describes him has “an exotic bird kind of guy.” In many ways this is true. Armisen’s brand of comedy is beyond the norm of what most other comedians do, and this episode gives a brief insight as to why and how that is.
27. Jimmy Fallon: “The Unsinkable Legend”
An episode so packed that it had to be split into two parts. But did it though? One episode is Jerry finding a location to detach his boat, but the meatier of the two does what Fallon fans want by providing a healthy dose of smiles. The content is like a timeline of Fallon’s life, discussing his SNL days to his current Tonight Show ones.
26. Bob Einstein: “Unusable On The Internet”
I mentioned earlier in the list that Howard Stern’s sarcasm came off as mean spirited. But Bob Einstein finds a way to be completely sarcastic in a fun and silly way. The bit where Einstein actually leaves the car mid-episode is one of the show’s funniest moments.
25. Bob Einstein: “It’s Not So Funny When It’s Your Mother”
This Bob Einstein episode is even more entertaining than the last. Jerry adds a whole “will he, won’t he” element about giving him his brand new Acura as a gift if the interview goes well. There’s a reason Einstein is Jerry’s first repeat guest in the series.
24. Steve Harvey: “Always Do The Banana Joke First”
I’m admittedly not the biggest Steve Harvey fan, but listening to Jerry talk about what makes Harvey a good comedian made me want to reconsider that thought. The two talk about the break down of jokes and how it’s impossible to teach a comedy class.
23. Patton Oswalt: “How Would You Kill Superman?”
I’m convinced Patton Oswalt could sell anything to anyone. He speaks so passionately about any and all topics that he can draw you in with any sort of fact or story. Which comes in handy when dealing with a broken down DeLorean and describing favorite downtown locations.
22. David Letterman: “I Like Kettlecorn”
All it takes to get David Letterman to open up about noteworthy Late Show stories is a bag of freshly popped kettle corn. Like Leno’s episode, Letterman thinks back on specific Late Show moments that stick out to him. Jerry comes off super engaged, and as a result, so are we.
21. Bill Maher: “The Comedy Team Of Smug And Arrogant”
Anyone who has ever watched Real Time With Bill Maher knows he can be a little much. But this episode shows us a different side to Maher—a gentler side. So much so that Jerry seems like the darker of the two when chatting about dying ‘70s rock stars.
20. Lorne Michaels: “Everybody Likes To See The Monkey”
A lot of comedians today owe their careers to Lorne Michaels for giving them their big break on SNL. Nobody has more insightful things to say about performing live comedy than him. Even if he isn’t a comedian himself, he respects the art all the same.
19. Michael Richards: “It’s Bubbly Time, Jerry”
You may still hate him for his offensive comments on stage years ago, but that’s all the more reason to check out this episode. Richards takes the time he has to show vulnerability and share with Jerry what he felt that night and how he has continued feeling since. It’s undeniably touching.
18. Margaret Cho: “You Can Go Cho Again”
Margaret Cho uses her unique voice to address darker issues. She is a survivor of sexual abuse, and talks about that a lot in her act, which according to her, upsets people. But it’s this personal side of her comedy that drew Jerry to her in the first place.
17. Chris Rock: “Kids Need Bullying”
With Rock, it’s all about the company you surround yourself with. He says that even a hot dog with an interesting person is a good time, which is actually what you get when spending this episode with Rock: a good time with an interesting man.
16. Tina Fey: “Fences Are My Purview”
Any opportunity you can get to watch the great Tina Fey try a strange wheat puff milkshake, you take it! Prepare to be inspired listening to Fey talk about her ambitions and goals, even after she’s accomplished so much already.
15. John Oliver: “What Kind Of Human Animal Would Do This?”
Even on a bleak rainy day, like the one featured here, John Oliver can be a shiny bright light. He isn’t afraid to talk in depth about times he’s bombed on stage or said the wrong thing about his wife on TV. In getting personal, he explains the important internal logic of comedy.
14. Trevor Noah: “That’s The Whole Point Of Apartheid, Jerry”
A history lesson in the South Africa comedy scene. Trevor Noah shares his personal journey that no other comedian on the show can replicate. It helps that Jerry seems interested and fully invested in Trevor’s stories, as anybody who watches this episode will be.
13. Robert Klein: “Opera Pimp”
Not a friend, not a stranger, but instead a personal hero of Jerry’s. Robert Klein started a whole new wave of stand-up comedy in the 1960s and we now get to hear all about. After a tour through his home, Klein might just become one of your favorites too.
12. Sarah Jessica Parker: “A Little Hyper-Aware”
Ever wanted to hear Jerry sing a musical bit? Of course you did, and with this episode you can! Not only that, but Parker’s bubbly personality practically leaps off the screen. If guest enthusiasm were a competition, she would crush just about everyone.
11. Jon Stewart: “The Sound Of Virginity”
Pre-Daily Show Stewart is not one that we’re all familiar with, but it’s a fascinating part of his career none the less. The two get into the details of how Stewart found his voice in the political satire scene, and how their work schedule fits the natural rhythms of doing comedy.
10. Kristen Wiig: “The Volvo-ness”
Delightful is a word that comes to mind when watching this episode. It’s not because of the quaint little bookstore they walk into, but because of Wiig herself. She’s a natural conversationalist full of interesting stories about her start in LA and her early SNL days.
9. Will Ferrell: “Mr. Ferrell, For The Last Time, We’re Going To Ask You To Put The Cigar Out!”
is somebody who can be funny in even the most simplistic of situations. He’s introduced by playing on a swing set like a young child and it’s impossible not to be won over. You’ll get to learn all about his SNL audition, which I would have paid anything to have been in the room for.
8. George Wallace: “Two Polish Airline Pilots”
Stand-up legend George Wallace is overflowing with energy here. He’ll start a conversation with anybody and will even shout questions in a crowded room for a laugh. We also get to see the backstage lead up to one of his performances, where even Jerry gets in on the action.
7. Barack Obama: “Just Tell Him You’re The President”
In another life, former President Barack Obama probably could have been a successful comedian. He has the delivery down and laid back sense of humor that people feel at ease listening to. Getting an exclusive tour of The White House is reason enough to put this episode of your radar.
6. Jim Carrey: “We Love Breathing What You’re Burning, Baby”
I miss Jim Carrey, you miss Jim Carrey, we all miss Jim Carrey. The old Jim Carrey, anyway. It’s been a long time since Carrey made a movie that made us cry with laughter like his mid-’90s work did. While this is only a fun sized return, it’s better than nothing. It’ll make you fall in love with his crazy antics all over again.
5. Julia Louis-Dreyfus: “I’ll Go If I Don’t Have To Talk”
Jerry and Louis-Dreyfus are such close friends that they practically finish each other’s sentences. They spend most of the time reminiscing about old Seinfeld inside jokes, as one would expect. It plays out like old friends who haven’t seen each other since college going “remember this, remember that!” For the Seinfeld enthusiasts, this is pure gold.
4. Garry Shandling: “It’s Great That Garry Shandling Is Still Alive”
The fact that this episode aired only two months before Shandling’s tragic death and the title of it is “It’s Great That Garry Shandling s Still Alive” is freaky. But get past the coincidence, and you’ll find yourself on a comedic ride through the famous Comedy Store while hearing old Tonight Show stories.
3. Louis C.K.: “Comedy, Sex And The Blue Numbers”
Anyone who has watched even one of C.K.’s stand-up specials knows he is a master storyteller, and this episode is further proof. The story he tells about his boat being stuck at sea is just as good as anything he’s told on stage. Equal parts hilarious and insightful to watch.
2. Steve Martin: “If You See This On A Toilet Seat, Don’t Sit Down”
Despite an awkward broken down car moment, this is one of those episodes that defines the show. Jerry takes an in-depth journey down the rabbit hole that is Martin’s historic career, covering everything from comedic timing, bombing on stage and feeling free while performing.
1. Judd Apatow: “Escape From Syosset”
The best, most well rounded episode is the one with the biggest comedy nerd to appear on the show. Judd Apatow talks comedy like your jock college roommate would talk sports. He shows off his comedic memorabilia, explains why he returned to stand-up, and talks about their dear friend Garry Shandling.
Christian Becker is a writer and improv comedy performer in New York City. Follow him on Twitter @TheAmazingBeck.