Questlove: The Art of Self-Sabotage

Mike Birbiglia's Working It Out

Mike Birbiglia's Working It Out podcast

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4.8 • 4K Ratings

🗓️ 6 October 2025

⏱️ 57 minutes

🔗️ Recording | iTunes | RSS

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Summary

Best of WIO: Questlove (Recorded April 2025) The legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.

Transcript

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0:00.0	who are you jealous of?
0:03.7	Oh, God.
0:05.2	Do I have to give a proper noun?
0:08.7	I don't know.
0:10.4	Yeah.
0:11.0	The follow-up question is,
0:13.3	who are you jealous of that you thought of,
0:15.3	but you didn't say?
0:26.1	That is the voice of the great Amir Thompson, aka Quest Love.
0:30.0	One of my all-time favorite episodes, we are re-airing this from April.
0:32.4	It's a great conversation about creativity.
0:41.9	I found it super inspiring, and so did our listeners, which is why we are re-airing it today in case people miss it the first time or want to recommend it to friends.
0:53.8	You can see Questlove in Spinal Tap 2, which is in theaters now. What a sentence. He has had an amazing year. He was nominated for an Emmy for his documentary, Sly Lives, who's nominated for the S&L music
0:56.3	documentary, which is unbelievably good. I mean, actually, the Sly one is unbelievably good, too.
1:02.0	I mean, these are great, great pieces to watch. So a lot of stuff, if you haven't caught up
1:08.2	on Questlove stuff, watch all of that this week. Special announcement we have launched Working It Out Premium. This is an ad-free version of the podcast, which is always available. Almost 190 episodes available on Apple Podcasts. And when you subscribe to Working It Out Premium, you get three things. You get an ad-free version of the podcast, no ads. You support the show,
1:28.3	which means a lot to us. And number three, bonus content. This week, we are releasing our first
1:34.4	ever bonus content episode where I tag people's jokes. People sent in their jokes last week
1:40.8	on Instagram. They send voice memos. It's really, really, really good jokes.
1:47.0	But we have a great talk with Questlove today, massive fan of Questlove. We talked about his music,
1:53.2	his documentaries about SNL and Slice Stone. Enjoy my conversation with the great Questlove.
1:59.4	We're working it. join my conversation with the great Questlove.
	...

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