How Long

a year ago ep. 382 feat. Smiley 01:06:31

Smiley is a rapper from Toronto, currently living in Los Angeles. We chat about mid chicks and vocal fry, when you CEO too hard, Dimes Square is on Google Maps, Rolling Loud vibe report, when you go on the scariest ride at the amusement park first, everything else is easy, is easier to work out in LA than Toronto because of all the selfies, how much his gym and sauna lifestyle mirrors ours, Smiley is OCD when it comes to cleaning, his love of cooking, his weight loss journey, where he’s hanging out in LA, Smiley moves older than most people his age, when people think you’re goofy, undercover cops at Popeyes, getting out on parole, how working with Drake has helped him beyond music, investing in real estate, and we play top three prescription pills.


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About us

How Long Gone is a bi-coastal elite podcast from old friends and podcast professionals, Chris Black and Jason Stewart. CB and TJ deliver their takes on pop culture, fashion, music, and more.

A grainy photograph features How Long Gone hosts Chris Black and Jason Stewart reclining in the grass before a fountain containing a large golden statue of a leaping man.

Tour Dates

12/02/23 New York, NY, Webster Hall
12/08/23 Boston, MA, The Wilbur, with Kevin Morby


Check out our show on Spotify and Podcasts
Follow @donetodeath on Twitter & Instagram
Follow @themjeans on Twitter & Instagram
Press: Grub Street, Interview, New York Times, Vogue, WWD


Live Event Booking: High Road Touring
Label: Jagjaguwar

All episodes

576 – 001
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New episodes every Monday, Wednesday, and Friday