Rob Sheffield ’88 is a columnist and contributing editor for Rolling Stone, where he writes about music, TV and pop culture. He started at the magazine in 1997, following freelance work for publications like Spin and the Village Voice. A self-proclaimed lover of “pop trash,” Sheffield is a fan of both Kanye West and Taylor Swift. He is the author of the memoirs “Love Is a Mix Tape: Love and Loss, One Song at a Time” and “Talking to Girls About Duran Duran: One Young Man’s Quest for True Love and a Cooler Haircut.” His latest book, “Turn Around Bright Eyes,” is about love, heartbreak and the power of karaoke. WEEKEND sat down with him to talk about music and writing, Prince and Miley Cyrus.

Q. How did you get into writing about music?

A. At Yale, I used to love to sitting around the Stiles dining hall and blathering about it with my friends. It being the 80s, we argued about Prince all the time. I was the class of ’88, so we were the class that entered with Purple Rain and went out with Love Sexy. [Prince] had an album come out every year, and every year was a drastic departure from the last. We would argue about whether Prince lost it this year or if he had ascended to new levels of Prince-osity.

At Yale, so many of my friends were in bands. Pierson B11 was basically a boiler room converted into a music space. Lots of student bands would play there, and it was fantastic to see friends of mine from Yale and from New Haven just picking up instruments and doing it. That was mind-blowing to me.

A lot of friendships formed over conversations about all these different kinds of music. One of the first people I met at Yale was Marc Weidenbaum ’88. We were standing in line. He was wearing an REM shirt, and we just started arguing about REM. Another one of my close friends is Andrew Jeffey ’88. He’s an astrophysicicist at the University of London, but we still talk about music all the time. It’s funny — 30 years later, and we’re still really close friends, and we still have these same arguments, except now it’s over text and Twitter. I also worked on an undergrad music publication back then called Nadine (It was named after the Chuck Berry song) founded by Joe Levy ’86, now editor of Billboard Magazine, and Julian Dibbell ’86. I’m still friends with both of them. It was working on Nadine that I started writing all these batshit insane ideas about music.

Q. Your latest book, “Turn Around Bright Eyes,” talks a lot about karaoke. What is it about karaoke that you like so much?

A. For me, karaoke allows anyone to participate in music, even those of us with no talent whatsoever. I’m fascinated with the way karaoke lets people shed their inhibitions about sharing music. “Let their inhibitions run wild,” as Rod Stweart would say. It’s funny — you go to a karaoke place and see all these people who can’t sing get up, but they’re getting up and doing it in front of strangers, and some kind of fierceness comes out of them that isn’t necessarily there in everyday life. For me, it’s exciting to be part of that, and it’s something I wanted to write about. Basically, what I always end up writing about is music and human emotions — how music tells us about human relationships, but also how music is a part of them. It’s funny how technology is always changing but that fundamental urge to share music is always the same, so my first book was about mix tapes; this one is about karaoke. It’s the same urge to share music with people.

Q. Any favorite karaoke songs?

A. “Total Eclipse of the Heart”— it’s a jam of mine. “Ziggi Stardust” is another one.

Q. Why do you like writing memoirs about music?

A. The stuff I write about are the things I really want to understand better. So my books are basically about music and love — those are the two mysteries that I always want to understand better. I just keep coming back to the idea that you can figure out all the mysteries of love by using music.

All the relationships that I write about in these books — my life as a husband, as a son, as a friend — all of those relationships are inflected with music for me. All those moments have a soundtrack, and it’s funny that I’ll remember a song and it’ll trigger a memory. It’s like you’ll be sitting in the car and a song will come up on the radio that triggers these memories, all these really intense feelings. And so that’ll be what drives the book for me, even if the books are strictly about music.

Q. What is one of these songs?

A. There’s a song by Rod Stewart that I heard yesterday at Starbucks. It’s called “You Wear it Well.” I loved this song as a little boy. It’s about adult heartbreak, one of those things I had no concept of back then. I hear it now, and it’s a completely different song because you know, I’ve been through some of the things the song is about. It’s weird how some music follows you through your life.

Q. In Rolling Stone, you wrote about Miley Cyrus’s appearance at the Video Music Awards. What did you think of her performance?

A. The article was about how pop music has this undiminished power to polarize people. I was expecting the show to be kind of dull. I think everyone was expecting it to be kind of dull. But then Miley performed, and it’s one of those things when you’re thinking, “Clearly this is insane, but is this insane-awesome or insane-terrible?” I came down strongly on insane awesome. It’s something people still like to argue about. Nobody can predict that music is going to affect people like that, and that’s the thing I’ve always thought is fantastic about music: it’s capacity for surprise.

Q. What about it made you come down on the side of “insane-awesome”?

A. I liked the way the song has strong elements of sentimental 70s R&B. It was a really beautiful song in terms of the chords and production. It soars. It’s sweet, and it’s moving. But then the vocal is a dumbass party commando song, and it’s a fantastic karaoke song. I just thought it was really funny, really surprising.

Q. Do you have any favorite pop singers?

A. I’m really obsessed with the new Kanye West album. I’m more obsessed with this album than I have been with any in a whole. It’s a really amazing, super paranoid electro kind of record. Then at the last song end, it goes to this retrospective thing about falling in love. It’s full of surprises. Kanye West is kind of like Prince. He puts out an album every year, and it’s always different from the last one. He always keeps that kind of debate going, and the last song “Bound 2” just completely blows me away.

I also think Red, the Taylor Swift album that came out about a year ago, is this incredibly brilliant pop manifesto. The way she’s trying out all these different kinds of pop music—a lot of country, disco, arena rock. I love how she’ll have a song like “Red,” which is disco, but with banjos on it. That’s some serious next-school visionary stuff.

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