DETAILS: When was the first time someone told you that you had a great singing voice?
Josh Groban: I was very shy about the largeness of my voice. When you're 30 and you sing in a grand and chivalrous way, you can perform at Lincoln Center. When you're 14, it's the kind of thing you hide. It was the grunge era. I wanted to open my mouth and sound like Eddie Vedder, I didn't want to sound angelic. My parents never heard me sing until junior high, when I did the Gershwin song "'S Wonderful" at a school show. Afterward, my mom was in tears. Little did I know it would be the first of many times I made a mom cry.
DETAILS: Women do respond emotionally to your music. You've probably helped more guys get laid than Jack Daniel's.
Josh Groban: I hope that's true. I was on a date once, and the girl came over and was looking for music to play. We were having a glass of wine, and she played rough mixes of my new record and started dancing to it. I was like, "Don't do that. Groupie alert, groupie alert!" I can't get turned on by my own music.
DETAILS: How do you feel about the term popera, which has been applied to your songs?
Josh Groban: It irks me, because it trivializes something that's actually very difficult to do. It feels dismissive. My voice is classical in nature, but I've always viewed my music as pop, influenced by the arrangements of yesteryear, when big, open-throated singing was the popular style.
DETAILS: What's the most rock-star thing about you?
Josh Groban: As you can tell by my Mr. Rogers cardigan sweater, I take pride in being nerdy. But I love going out. I can't trash myself, because I have to protect my voice, but I'm not a prude either. In the 1970s, a rock-and-roll lifestyle would be snorting coke off a hooker. Now the rock stars I know are the healthiest people. "Oh, you get vitamin B-12 injections in the ass too?" The guy from Metallica has a yoga room. So the rock-and-roll thing is, I bought a Porsche. But the non-rock-and-roll thing is, the battery kept running down because I was on tour for so long I was never able to drive it.
DETAILS: Did you hear from Kanye West after singing his tweets on Jimmy Kimmel's show?
Josh Groban: No, I don't think he got the joke. Kanye lives in a phenomenal world all his own. But man, those tweets! If he doesn't know they're comedy gold, then God help him, truly.
DETAILS: Any chance you'll record those?
Josh Groban: During my shows, someone will shout, "Sing Kanye's tweets!" And I'll be like, "All right, I will. You asshole." It's always hysterical.
DETAILS: I follow you on Twitter, and you're way funnier than I would have thought, based on your music.
Josh Groban: In the same way Kimmel gave me an opportunity to be funny in a skit, Twitter gives me a chance to be myself when I'm not on stage. I not only like it, I've become addicted to it.
DETAILS: Speaking of tweets, you tweeted something nasty about Lindsay Lohan when she hosted Saturday Night Live.
Josh Groban: Was that bitchy? I just felt like, What is that person doing? It just didn't seem she had any comedic ability. I was jealous that she got to host SNL, which I love with a passion. And I was drunk. So between those thoughts and the delicious Lagavulin that was burning a hole in my stomach, I wrote a snarky tweet.
DETAILS: Is it true you're friends with Katy Perry?
Josh Groban: We're very good friends. We met before her first album was even released, and we hit it off because we're both goofballs.
DETAILS: Did you date her?
Josh Groban: No, not really.
DETAILS: "Not really"? It's simple, Josh: Did your tongue ever touch her tongue?
Josh Groban: [Laughs.] I'm not commenting on that. We might have skated on the line of dating.
DETAILS: But you did date January Jones, before she was on Mad Men.
Josh Groban: We dated for about two and a half years, and we were madly in love. It was definitely my longest relationship. I'd love to get into another serious relationship. I am a real romantic at heart.
DETAILS: You have a big role in the upcoming comedy Coffee Town. Are you playing a douchebag, as you did on Glee and in Crazy, Stupid, Love?
Josh Groban: I am, yeah. I play a disgruntled barista who's in a rock band and is angry at his customers. It's almost like Clerks in a coffee shop—we fuck with each other, drawing penises on coffee cups or whatever. They put the douchiest tattoos on me, like flames coming up one arm, plus a goatee, eyeliner, and a studded leather bracelet.
DETAILS: When you play a douchebag, who's your model?
Josh Groban: I tried to get a [Creed singer] Scott Stapp energy, kind of nineties and snarly. I felt that if I could get a "With Arms Wide Open" music-video vibe behind the coffee counter, that would be successful.
DETAILS: How do you make your live shows fun when you're singing such serious music?
Josh Groban: I go into the audience. When you put the microphone in front of someone, you never know what's going to happen. I talked to a guy one night, and he said, "We're happy you came to Indianapolis." Then he said, "You mind if I say one more thing?" And he pulls something out of his pocket. I thought he was going to shoot me. Honestly. I thought he was going to say, "One more thing—you deserve to die. Bam, bee-yotch!" But he pulled out a ring and proposed to his girlfriend. That's happened two or three times, and it always puts a nice mood in the room. Then I make a fart joke.