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.

Tiffany 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 much in common you wouldn’t expect, so tune into 21 Questions now.

21 Questions is made in partnership with Fairmont Hotels and Resorts. This episode was filmed in Santa Monica California at the stunningly beautiful Fairmont Miramar Hotel & Bungalows.

21 Questions is proudly made by by coastal and Project 10.

On this week’s episode of 21 Questions, Madison reflects on friendship, growth, and the people who shape us along the way.

She shares what it was like growing up without a large circle, and how her experience filming the movie Champions helped her build a true group of lifelong friends. At the heart of it all is the importance of having people you can count on. It’s something Madison deeply values, and something she’s committed to creating within her own community, too.

In this episode, Madison and Producer Sylvia also chat about love! And what it means to have a partner who supports you fully, someone who hypes you up, stands by you, and shows up for you on your best days and your hardest ones.

And, of course, there’s music. Madison shares how music is her love language - a universal way she connects with others, often through thoughtfully curated playlists. For her, music isn’t just a passion, it’s a powerful way to deepen relationships and bring people closer together.

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

This is the first ever LIVE episode of 21 Questions coming to you from South by Southwest in Austin Texas!!

Madison knows first hand how fun it is to people wrong so today her and Ashley Callingbull are going to talk all about turning adversity into success.

Ashley is an actress, model, host, international public speaker and First Nations activist. She’s done everything from competing on The Amazing Race Canada, to winning Miss Universe Canada, to speaking at Harvard AND being the first ever First Nations Sports Illustrated model.

Ashley is a true change maker. She’s been named Canada’s Top 20 Under 30, the Top 10 Power Women, Indspire’s Youth First Nations Award, the Esquao Awards’ Circle of Honour, a UN Role Model Award, and the Queen Elizabeth II Platinum Jubilee Medal.

Ashley knows that your dreams are worth chasing, no matter what anyone else thinks, and we couldn’t agree more.

This is 21 Questions live from South by South West.

This episode was filmed at SXSW and in the heart of South by Southwest and at the Fairmont Austin.

21 Questions is made in partnership with Fairmont Hotels & Resorts.

21 Questions is proudly made by by coastal and Project 10.