LAS VEGAS, NV - SEPTEMBER 18: Singer Sam Smith performs onstage at the 2015 iHeartRadio Music Festival at MGM Grand Garden Ar
Kevin Mazur/WireImage

Today Sam Smith presents his deluxe re-release of his May 2014 debut album In the Lonely Hour. Subtitled Drowning Shadows Edition, it's got a second disc featuring nine extra songs, including a live version of his Disclosure collaboration "Latch," a Mary J. Blige–featuring "Stay With Me," an A$AP Rocky–aided "I'm Not the Only One" and the marvelously John Legend–ified "Lay Me Down."

Oh, and a cover of Amy Winehouse's "Love Is a Losing Game" Earlier this week Smith dubbed "Drowning Shadows" the "saddest song I've ever written." But his aching voice paired with a tune reminding us of the tragic loss of Winehouse at the age of 27 is pretty heart-wrenching:

Vulture notes that Smith has had a cover of Winehouse's "Tears Dry on Their Own" in his repertoire for some time. Here's what he told the BBC about his choice to cover "Love Is a Losing Game":

“People forget sometimes my age, I think, because I was 11 years old when Frank came out. And I remember sitting in my car, 11 years old, and that album came out. And that album has really shaped me as an artist and just my views on music and my relationship with music, lyrically. Seeing that film just brought me back to that moment of being of 11 years old; just her rawness on such beautiful chords, on such expensive chords, it’s just amazing.”

Spin the entire In the Lonely Hour (Drowning Shadows Edition) on Spotify and/or grab it on iTunes, and get the scoop on the Amy Winehouse biopic now in development.