21 Questions

05/17/2026

When you have Tiffany Haddish in your corner, anything is possible! But seriously, having John Legend as a guest on 21 Questions would be such a full circle moment! Because it really did all start the second I was brave enough to press post on that YouTube video of me singing a cover of his song ‘All Of Me!’ No matter how much time goes by, that will always be one of my all time favorite songs. And sharing the story with him about how his music literally changed my life? That would be the dream for real! John, if you’re listening... my girl Tiffany and I are patiently waiting to hear from you 😉❤️

Tune in to this week’s episode here: https://linktr.ee/21questionspodcast

JohnLegend

05/16/2026

We played two truths and a lie this week and one of the answers had Tiffany in shock. Madison dropped some truly unhinged news, chocolate was betrayed, and Madison... we have questions. Full comedy in this week's episode at the link in bio.

21 Questions is proudly produced by by coastal and Project 10, in partnership with Fairmont Hotels & Resorts. This episode was filmed in Santa Monica California at the stunningly beautiful Fairmont Miramar Hotel & Bungalows.

Watch or listen to the full episode here: https://linktr.ee/21questionspodcast

05/15/2026

So much work goes into podcast filming days and it honestly starts way before the cameras start to roll. From my days researching and prepping guests to glam, set prep, to making sure our shots are perfect and our sound is clear, to getting behind the scenes content for socials... all the way to the moment we actually start filming!

I’m beyond lucky to have such a talented team supporting me to bring each episode to life. Thanks to all of them for always crushing it! I couldn’t be more thankful for all of you if I tried.

This episode was SO FUN! had us all laughing, even my team was having a hard time keeping it together 😂Tiffany and I talk about things I never thought we would get into and I have a feeling you’re going to love it. I can’t wait for you to get in on the all the action!

Watch or listen to our episode here: https://linktr.ee/21questionspodcast ❤️

05/14/2026

Today Madison sits down for a bold, hilarious, and totally unfiltered conversation with Tiffany Haddish.

Just like Madison, Tiffany is someone who dreamed big early on and is making her success happen on her own terms. Tiffany went from doing stand-up and grinding through the comedy scene to becoming one of the most recognizable voices in entertainment, breaking through in a massive way with the movie Girls Trip. She is also a bestselling author, a producer, and a powerhouse performer who was also the first ever female African American Stand Up comic to host Saturday Night Live.

Madison and Tiffany share so many things in common, it even surprised them! Tune into 21 Questions now.

21 Questions is proudly produced by by coastal and Project 10, in partnership with Fairmont Hotels & Resorts. This episode was filmed in Santa Monica California at the stunningly beautiful Fairmont Miramar Hotel & Bungalows.

Watch or listen to the full episode here: https://linktr.ee/21questionspodcast

05/13/2026

"Does it move my soul?" — that's the lens we're looking at everything through from here on out.

Tomorrow on 21 Questions, a brand new episode with the one and only Tiffany Haddish. Madison and Tiffany go deep but you also better be prepared to laugh. We definitely did.

21 Questions is proudly produced by by coastal and Project 10, in partnership with Fairmont Hotels & ResortsResorts. This episode was filmed in Santa Monica California at the stunningly beautiful Fairmont Miramar Hotel & Bungalows.

05/07/2026

05/06/2026

An all-new episode of 21 Questions out now!

It’s no secret Madison LOVES music. She shares how it’s her love language, the way she connects with others and how she’s the go-to playlist maker for all her friends. Cue the Bruno Mars dance party.

21 Questions is proudly produced by by coastal and Project 10, in partnership with .

05/06/2026

An all-new episode of 21 Questions out now!

It's no secret Madison LOVES music. She shares how it's her love language, the way she connects with others and how she's the go-to playlist maker for all her friends. Cue the Bruno Mars dance party.

21 Questions is proudly produced by by coastal and Project 10, in partnership with Fairmont Hotels & Resorts.

Watch or listen to the full episode here: https://linktr.ee/21questionspodcast ❤️

05/05/2026

When Madison was younger, she didn't have a large circle of friends. In tomorrow's brand new episiode of 21 Questions, she opens up about how the friendships she's made through her experiences with Best Buddies and the movie Champions have helped her find people who truly understand her.

21 Questions is proudly produced by by coastal and Project 10, in partnership with Fairmont Hotels & Resorts.

05/01/2026

Don't you love when people have hidden talents?! Ashley Callingbull's Gollum impression is one I didn't know I needed but it's SO good. 😂 Seriously though, Ashley Callingbull has a pretty cool story about how she used doing impressions to help get her into acting!

Filming this episode live at SXSW was a full-circle moment for me. I remember sitting in the audience last year, watching Brené Brown and Andy Roddick record their podcast and leaving so inspired… I wanted to be on that stage and this year we made it happen.

Watch or listen here: https://linktr.ee/21questionspodcast ❤️