Conan O’Brien’s five best podcast episodes from season one

We count down the top five episodes from season one of the Conan O’Brien Needs a Friend podcast.

Conan O’Brien may have found a second (or third, or fourth) calling as a podcast host. Season one of “Conan O’Brien Needs a Friend” was an undisputed hit and one of the best comedy podcasts to be found anywhere.

The launch of “Conan O’Brien Needs a Friend” came during a number of announcements from Team Coco. Much of the attention went to the new format for Conan that saw the show move to a half-hour format. If anyone thought that signaled the beginning of the end of O’Brien’s late night tenure, they were sorely mistaken.

Instead, O’Brien and his team have continued to evolve and reinvent the show. Helping achieve that goal was the podcast, which O’Brien himself admitted was much more enjoyable than he anticipated. That may surprise some fans given O’Brien’s intelligence and interview skills. But podcasting is certainly different than hosting a late night talk show.

“Conan O’Brien Needs a Friend” was also aided by producer Matt Gourley and co-host Sona Movsesian. The three displayed an effortless chemistry right from the start and made each episode a must-listen regardless of the guest.

But the guests were also a major reason why O’Brien’s podcast was a hit. With just under 40 episodes, the show boasted a lineup of guests that other shows could only hope to book over years, not months. What other show has Michelle Obama, Julia Louis-Dreyfus, and Howard Stern in a matter of a couple months?

Season one recently came to an end. There are still mini episodes available featuring O’Brien chatting with Dana Carvey that make for a fantastic listen. To recap season one, Last Night On has picked its top five episodes. Let us know what you think!

5. Jimmy Kimmel

Of course a site dedicated to late night television is going to pay special attention when Conan O’Brien is interviewing another late night host. But no matter what, this conversation was an insightful one for fans.

For starters, it was the first (and probably only) instance of a guest inviting himself on to the podcast. O’Brien reveals that Kimmel sent an email saying that he would love to do the podcast without needing an invitation.

It worked out for the best as Kimmel was actually the one to get O’Brien to open up about his career. We hear how O’Brien’s attitude about late night competition has evolved over the years and why he doesn’t plan on stopping any time soon.

We also found out that hosting a show isn’t as fun as you’d think for Jimmy Kimmel. He admitted to rarely having fun but isn’t exactly sure what else he would do if he walked away. Fans don’t have to worry about that considering Kimmel recently signed an extension with ABC.

4. Kristen Bell

Kristen Bell was the guest for the second episode of “Conan O’Brien Needs a Friend.” But the interview set the stage for what the podcast could be moving forward.

Bell’s visit came after the first episode featured an in-depth discussion with Will Ferrell about all things comedy. Conan O’Brien’s conversation with Bell was something much different but still very entertaining.

The early episodes more closely adhered to the framework of O’Brien looking to make friends. So with that in mind, things got a little more personal and a little therapeutic between O’Brien and Bell. Fans were able to hear a different side of O’Brien that perhaps they weren’t expecting to get on the podcast.

Bell’s willingness to talk about sensitive subjects and O’Brien’s willingness to be open helped make similar conversations a possibility in future episodes.

3. Mila Kunis

The Mila Kunis episode lands on this list because of just how off the rails things got seemingly out of nowhere. It wasn’t often on the podcast that a guest was crying from laughing and had Conan O’Brien, Sona Movsesian, and Matt Gourley all hysterical.

Fans of Kunis were not surprised to hear she was just as down to earth on the podcast as she is in every other interview she’s done. What they probably didn’t see coming was the actress admitting to a criminal past that included making bootleg t-shirts and intentionally crashing cars.

If Conan O’Brien makes a point to declare a episode the craziest one yet, then there is a pretty good chance it deserves to be on a list like this one. Here’s hoping season two features a conversation with Ashton Kutcher that includes a surprise appearance like Kunis to repay the favor.

2. Howard Stern

From the outside, it wouldn’t appear as though Conan O’Brien and Howard Stern have all that much in common or are compatible from a comedy perspective. But whenever the two get together and talk, it is a must-listen event.

Stern recently stated that his interview with Conan O’Brien in 2015 was the favorite one he had ever done. He went in thinking one thing about O’Brien and came out with a completely different mindset after O’Brien opened up about anxiety, depression, and his career.

That conversation was given an unofficial part two when Stern came on O’Brien’s podcast in May. Stern proved why he is one of the best interviewers in all of media by managing to ask O’Brien questions as if Stern was the host.

There is clearly a mutual admiration and respect between the two and that comes through loud and clear on the podcast. This episode above all others felt like a private conversation between two people, giving it a level of intimacy that listeners have to appreciate.

1. Stephen Colbert

The late night bias may be at work here but the Stephen Colbert episode was the highlight of season one. Conan O’Brien finished the episode by concluding that he and Colbert were long lost brothers.

This episode best represents the what makes “Conan O’Brien Needs a Friend” such a fantastic podcast. It offers a behind-the-scenes look at comedy, as was explored in the first episode with Will Ferrell. It addresses some real issues related to anxiety, guilt, and mental health that have popped up on other episodes. And it also has sillier, lighter moments that prove above all else, O’Brien wants to make people laugh.

Which episode of “Conan O’Brien Needs a Friend” was your favorite? How would you rank your top five episodes? Let us know in the comments below. Keep checking Last Night On for updates and news from Conan O’Brien and the rest of late night.