When Matt Nathanson started writing his new record, he had a vision. He wanted it to be political. He wanted it to be uplifting. He wanted to inspire his listeners to see a brighter future.

The songs that came out of him had other plans.

Sings His Sad Heart, the follow-up to Nathanson’s 2015 LP Show Me Your Fangs, is personal instead of political, sad instead of uplifting, and lost in thoughts about the past instead of looking forward to the future. It is a complete contradiction of the album that Nathanson wanted to make. And yet, it’s also the most at home he’s sounded on a record since 2010’s breezy Modern Love.

Then again, Nathanson has always been an artist defined by his contradictions. He’s a riotously funny and jovial live performer who makes crushingly sad records. He’s a guy who exudes confidence and charisma onstage but admits he isn’t very confident as an artist. And he’s a songwriter who’d name the happiest song on his record “Sadness.”

When I spoke to Nathanson in August, I called him “the most nostalgic guy in the room.” It’s a role I often find myself playing: the guy who digs through TimeHop every day and sends pictures and “remember this?” messages to old friends, or the guy who spends entirely too much time thinking about people he lost touch with, wondering if they ever think of him too.

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I got to speak on the phone with the ever-amusing and ultra-talented Matt Nathanson. In our interview, Nathanson described the disjointed but ultimately satisfying nature of his brand new album, Show Me Your Fangs. We also discussed the unpredictable audience-request format of Nathanson’s current tour, how some of the best records have “great topography” instead of being thematically or musically cohesive, and how elements of hip-hop and R&B have slowly crept into Nathanson’s singer/songwriter-oriented music.

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