If there’s one thing we know about David Letterman (other than that he’s hilarious and smart and one of the best people in the world to fall asleep with), it’s that he loves country music and he LOVES Outlaw Country‘s Elizabeth Cook.

But Elizabeth isn’t the only country artist who Letterman has given an outlet to. He’s known for sharing the love by bringing artists like Jason Isbell, Ray Wylie Hubbard, Dale Watson and other country and Americana artists on Late Show. And where do you think he was first introduced to many of his favorites? The Wall Street Journal explains:

During his commute to Manhattan from North Salem, N.Y., he often listens to SiriusXM’s Outlaw Country channel. Jeremy Tepper, who oversees the channel and has followed Mr. Letterman for more than 30 years, says the host has had ‘a roots-music bent for a long time.’

And don’t forget Rolling Stone‘s similar credit to Outlaw Country for many of the artists Letterman has had on his show.

He found kindred spirits in Isbell and Cook, the latter of whom he first heard on SiriusXM’s Outlaw Country station, during his regular drives into the city from his Connecticut home. While Fallon makes viral videos with Justin Timberlake, Letterman was asking Isbell and Cook for just one more Van Zandt song. More than championing roots, Americana and folk, what makes the Late Show stand out is that it’s always been booked from a place of taste, not trends.

So to celebrate (mourn?) Letterman’s last episode on May 20, we’re looking back at all the times he welcomed Elizabeth to his show, tipping our hat to one of country music’s biggest fans.

Elizabeth’s first appearance on the Late Show.

Elizabeth’s second appearance on the Late Show.

Elizabeth performs If I Had My Way

Elizabeth performs Pale Blue Eyes

Elizabeth sings Tecumseh Valley with Jason Isbell

For a free 30-day trial, check out siriusxm.com/fbtrial

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