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Celebrating 100 Episodes of ‘How to Be Amazing with Michael Ian Black’

Here’s to 100 amazing episodes

How to Be Amazing with Michael Ian Black released its 100th episode today! The in-depth interview show, hosted by comedian Michael Ian Black, started in 2015. It takes listeners into the minds of some of today’s most fascinating celebrities and newsmakers to discuss the process of how they became, well, amazing.

We spoke to Michael and his team about their favorite episodes, notable “Amazing 5” choices (on every episode the guest picks five things they think are amazing under the categories of ‘Food,’ ‘Music,’ ‘Book,’ ‘TV,’ and ‘Miscellaneous’), and how they pick guests for the show.

For the 100th episode, Michael turns the tables on “the greatest interviewer of our time,” putting her in the interviewee chair.

Terry Gross is the iconic host of the public radio show Fresh Air, where for over 40 years she has interviewed approximately 13,000 guests. In this engrossing interview, she and Michael cover a huge range of topics about her life and the show, allowing us to get to know a bit about a voice we’re used to hearing ask all the questions.

Host Michael Ian Black

“We look for a balance of people who are household names and people who are not as well known but at the top of their field. There are always guests we try for but figure we don’t have a shot in hell of booking. We’re thrilled some have said yes! While we’re drawn to the performing arts, some of our most surprising and entertaining guests have been from the worlds of science, sports, and politics.”

Host Michael Ian Black’s Favorite Episodes

Episode #71: Eileen Myles

I liked talking with Eileen Myles because Eileen just feels so confident and cool. When I meet somebody who seems to understand who exactly who they are and has a passion for their work and an excitement about sharing themself and their work, I get into it.

Episode #88: Giada De Laurentiis

Michael Ian Black and Giada De Laurentiis

Giada De Laurentiis surprised me with how open she was. For some reason, I expected her to be a much more guarded, careful personality, but we had a great freewheeling talk about her life, food, and her vision.

Editor’s Note: Giada chose yoga as her miscellaneous choice during her “Amazing 5,” along with Ina Garten and Krista Tippett, host of “On Being.”

Episode #92: Jay and Mark Duplass

The only time I feel like we ever nailed a live interview was with the Duplass Brothers, Jay and Mark. They were so fun to talk to, incredibly thoughtful about their creative partnership and how they navigated sibling rivalries and the normal pressures that come from working so closely with somebody else.

Co-Producer Mary Shimkin’s Favorites

Episode #7: Carl Tanner

There are a few episodes where you may not know the person, but he or she just has the most amazing life story that you listen with your mouth open for the entire show. I’d say one of my favorites in this category is truck driver to bounty hunter to top opera singer, Carl Tanner, who was such a fun guest and great storyteller.

Episode #67: Ina Garten

In the category of long shot asks, I love the interview with the great Ina Garten. She was a complete delight and has such an inspiring story about going after a life that makes you happy versus just collecting a paycheck. Her use of a swear words didn’t even register with us, but her fans loved it, according to their response on Twitter. Fun fact, she and Michael have become friends since that interview and hang out occasionally. How great is that?

Episode #100: Terry Gross

You never know if someone is going to be a good interview, especially when she is used to asking the questions, but Terry Gross was genuine, revealing and generous with her time and herself. It’s one of those conversations that was so engrossing and intimate, I ended up running an extra two miles while listening without realizing it. So thank you, Terry!

Co-Producer Jennifer Brennan’s Favorites

Episode #2 Lin-Manuel Miranda

It is so fun to go back and listen to the super talented Lin-Manuel Miranda talk about Hamilton before it became a international phenomenon. He was so genuine, charming and thoughtful. It was inspiring to hear about his process. Also, I think this might be the only episode where Michael raps and I absolutely love that moment.

There are two episodes that are noted time and again for their big reveals, and I still think they are two of the best episodes we’ve done.

Episodes #19 and #20: David Sedaris

Sedaris was always on the top of our big wish list, so when he came to the studio we were excited, and he didn’t disappoint. What we didn’t expect was for him to tell Michael that he wished people would be more upfront about how much money they make, which, of course, allowed Michael to ask David how much money he makes. You’ll have to listen to hear his response.

Episode #38: Tim Gunn

Michael Ian Black and Tim Gunn

The other guest was Tim Gunn. About half way through his interview he revealed something about his early life that made all of us gasp, including Michael. Tim was so raw, personal and honest in a way most famous people never allow themselves to be. It was an amazing episode.

Editors Note: Fun fact, Tim Gunn revealed during his “Amazing 5" that he loves fencing, and Variations on a Theme by Mozart” by Chopin.

Editor Robin Linn’s Favorite Episodes

Episode #27: Audra McDonald

Audra McDonald is a personal favorite because I was able to have fun and work with an immense catalog of music: Porgy & Bess, Billie Holiday and The Sound of Music, not to mention clips from plays like A Raisin in the Sun. Audra also got to reveal her sense of humor and her own moments of humility and self-consciousness, which somehow reveal why she’s amazing.

Editor’s Note: Audra McDonald chose the “Hamilton” soundtrack during her “Amazing 5,” and on a recent episode #99, Jose Antonio Vargas chose Audra McDonald’s live album “Sing Happy” .

Episode #23: Dan Harris

As more and more people in different professions look to meditation for its healing power, I point them to Harris’ book and this interview, which I think smartly captures how one can have reverence for self-help, without losing a healthy journalistic skepticism. Again, as an editor, Harris offered opportunities for great audio in the form of news and interview clips, and he recommended a beginner’s guide to meditation that I went on to purchase myself.

Editor’s Note: On Josh Groban’s episode during “Amazing 5,” he chose Dan Harris’ book “Found Self-Help That Actually Works — A True Story.”

Editor Jason Saldanha’s Favorite Episodes

Episode #80: Tara Westover

Tara’s story is almost too fantastical to believe, but to hear her talk about her life in such a composed way, juxtaposed with the insanity of the story itself, was a great tension to interact with.

Episode #85: Nell Scovell

Nell Scovell and Michael Ian Black

Nell’s episode was a delight to edit because of the number of touch points she’s had in pop culture that I loved. She was honest, funny and someone I sought out to know more about after the interview.

Editor’s Note: Along with Audra McDonald, Nell also picked the “Hamilton” soundtrack as her music pick during “Amazing 5.”

Listen to How To Be Amazing by subscribing in Apple Podcasts, RadioPublic or wherever you get your podcasts.

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