Conan O’Brien Needs A Friend podcast ranking – the ten best episodes

You may know I have been a Conan O’Brien super fan for years. His remotes and skits are my go-to comfort videos after a bad day (I’m still holding out hope for a Dudez-a-Plenti with the same cast 20-plus years later) and his podcasts have been a new, unexpected success that has expanded Coco’s digital brand world-wide. The interviews with his guests are wide and varied, while the banter between Big Red and his assistant Sona (who might have the best laugh in the entertainment business) and podcast maestro Matt Gourley is light, waggish, and always humorous. Without further ado, put down your Peanut Butter Whiskey (apparently this a real thing), stop searching for streaming videos of krumping and how much Conan is worth since he invested so badly, because here is my completely nowhere close to being an authoritative opinion of my ten favorite Conan O’Brien Needs A Friend Podcast episodes.

Caro, Robert

As you know, yes, Conan went to Harvard. His interview with acclaimed biographer Robert Caro was an enlightening one. His fascination is with his subjects, who just like George Plimpton, put himself in the thick of it. Caro had such a hard time understanding Lyndon Johnson he moved to Johnson City, Texas to understand the type of poverty and loneliness LBJ came from. It’s a fascinating interview from an author who always gives a complete and fair treatment of his subjects.

Most Surprising Moment:

Caro cites a fact that’s jaw-dropping to me at least, that we dropped more bombs in Vietnam than we did in Germany during World War II.

Funniest Line:

Caro explains to Conan his response to his wife that they will be moving to a poor part of Texas to research a book on Johnson, and she responds, “Can’t you write a book about Napoleon?”

Carvey, Dana

Talk about your deep dives. I’m not sure what the good people of Ready Steady Cut’s average age of readership is, but back in the day no one was funnier than funnyman from Missoula. Carvey on Saturday Night Live was like a tornado stuck in a mason jar that was always ready to bust out, and no way to reign himself in until the camera cut to commercial. The same thing happened here as Conan and Carvey had so much fun this episode of the Conan O’Brien Needs A Friend podcast became a miniseries deep dive and a walk down memory lane.

Most Surprising Moment:

Listening to Carvey explain and perform the voices of the skit on how Bobby Kennedy tries to teach Adolph Hitler English in a bunker they hid in for a very long time play along with Elvis is as good as old-timey radio and ’90s SNL fusion as one can get (if you had to categorize it).

Funniest Line:

“Jon Lovitz is the kind of guy it took one day to get to know him and 20 years to believe it.”

-Dana Carvey to the room while discussing Lovitz secret catchphrase, “Jealous”

Fey, Tina

What I loved and even found almost exciting is the process that both SNL vets talk about; the writing process and grind of what it was like inside Saturday Night Live‘s writing room back in their respected days when it would cause the colorful peacock obsessive-compulsive disorder.

Most Surprising Moment:

Tina Fey’s husband, Emmy-winning composer Jeff Richmond, played the character “Russian Hat Guy” in his Late Night show.

Funniest Line:

“It was you or Roker, Roker passed.”

-Fey explaining the casting process of Conan playing her ex-boyfriend on 30 Rock for three and a half glorious minutes.

Hader, Bill

I know they are both from different generations, but there is something about Conan and Hader’s insanely comic personalities that makes me think they were both somehow separated at birth with the ever pale one with the river of fire hair just having a random genetic glitch. Listening to stories of going down memory lane and taking you inside the SNL writer’s room is as engrossing as the Conan O’Brien Needs a Friend podcast can get.

Most Surprising Moment:

Bill Hader, who appears to be one of the most confident and outgoing comedians on the planet, reveals his anxiety and trepidation when meeting his childhood heroes Conan O’Brien, Martin Short, and first performing on SNL.

Funniest Line:

Conan repeating, admitting butchering the line, quotes one of his favorite Jack Handy lines while giggling,

“I don’t know why everyone got so upset when I rushed up to give the president his chocolate gun.”

The actual Jack Handy Line:

“I think a good gift for the President is a chocolate revolver and since he is so busy, you probably have to run up to him real quick and give it to him.”

Kimmel, Jimmy

The fact that these two talk show legends get together and both are connected by a gigantic chin that changed the trajectories of their careers is like being a fly on the wall. Listening to both come to the conclusion of the false importance of it all is a direct relation to the number of late-night talk shows that are saturating the market at the moment this decade.

Most Surprising Moment:

Kimmel told the room that ABC actually came up to him to let him know they were going to approach Conan to replace him in 2004; much to the surprise of O’Brien, he said he was only approached by FOX. However, he does reveal that the same thing happened to him in 1993 and was told Greg Kinnear was tabbed to replace him.

Funniest Line:

“Look at my crotch-yeast.”

-Conan describing what’s going to happen to the beer that was spilled by Kimmel on his pants.

Eugene Levey and Catherine O’Hara

What I loved about this episode of the Conan O’Brien Needs A Friend podcast is the sound and laid-back voices of former veterans of SCTV. It brought me back to my summer days at my parent’s cottage on Lake Erie in Canada, vacationing with families from Toronto and Hamilton. They have a vernacular unique to that time and place which made me think how anyone I met from Canada was the funniest person I’ve ever met. It must be something in the water on that side of the imaginary border.

Most Surprising Moment:

Conan only discovered SCTV because of his brother’s fascination with television antennas in the ’70s finding a signal in Rhode Island all the way in Buffalo, NY. Okay, maybe not that surprising or interesting, but it’s my home town, so I need to slip it in.

Funniest Line:

“Conan, whatever you are doing to your face, do 20% more and then stop.”

-Conan repeating a line from fellow SCTV-cast member Martin Short.

Oswald, Patton

Listening to these two adorable comic nerds talk about their love for comedy, English comedies, just general nerd stuff, you could picture them easily sliding into a couple of guest spots in the comic book store in The Big Bang Theory. Oswald has fervent energy that you can’t help but enjoy, and that brings the best out of O’Brien.

Funniest Line #1:

“You want to sock my click?”

-Patton Oswald commenting on the egresses of the misspelling by porn spammers

Funniest Line #2:

“Just a couple of comic book nerds who can’t even think of who Eli Manning is.”

-Conan O’Brien

Maron, Marc

While Big Red says he thinks he and Maron share the same type of energy, I love this pairing because while Conan feeds off the audience’s energy, it almost feels Maron would rather be a curmudgeon in a dark corner. It’s an entertaining back and forth, with a crackle of very different personalities playing off each other as they “hide the hate and display the shame.”

Most Surprising Moment:

A bit between Conan and Sona on how he thinks he is just like Freddy Mercury while watching Bohemian Rhapsody is funny and inspired.

Funniest Line:

“You took me losing the tonight show, and made it about you.”

-Conan O’Brien

Gladwell, Malcolm

While I’m certain Conan is such a fan of The Tipping Point‘s author Malcolm Gladwell because he looks like he was clearly the inspiration for the Simpson’s villain Sideshow Bob, that doesn’t come up in this episode of the Conan O’Brien Needs A Friend podcast. What does is a funny, yet engaging and enlightening conversation of police overreach and brutality that comes with taking over the Sandra Bland and Amanda Knox cases.

Most Surprising Moment:

Gladwell’s story about trying to find his father’s famous friend who he chatted up about gardening in the lobby of the Mercer Hotel in 2004 and is the basis of his new book is an extraordinarily entertaining tale and is highlighted by O’Brien guessing it’s Michael Caine because the mystery man smelled of sandalwood and a coconut suntan lotion.

Funniest Line:

“We’ve forgotten the tropes of smoking a cigarette.”

-Gladwell explaining why a victim of police brutality used smoking to calm down and why an effective police officer needs to be a student of people.

Short, Martin

Martin Short’s ability to fill in the dead air (as Conan tries to think of a line Tom Hanks said to him about being a fly on the wall, Short chimes in, “When Princess Margaret gets married to Lord Snowdon?”) and well-timed, off-the-cuff remarks are one of the great simple pleasures of comedy late-night interviews and now podcasting. Other highlights from the interview in life, Victor Garber is Christ-Light, or Steve Martin is so pale he looks like something he snorted in the ’80s, the giggles that turn into belly-laughs do not stop anytime soon.

Most Surprising Moment:

Martin Short revealed that he based one of his most famous characters, Jimmy Glick, on his father’s mannerisms, almost unconsciously.

Funniest Line:

“You know what I love about touring with Marty Short? No Paparazzi.”

-Short repeating Steve Martin’s jab