Watch Josh Groban Tell the Ultimate Dad Joke

Long before he raised you up with several albums of operatic pop, Josh Groban had his eye on another career path: musical theater. After growing up catching touring companies in his hometown of Los Angeles, Groban attended a performing arts high school and summer camp (“It was kind of like Wet Hot American Summer with songs,” he jokes) with the dream of working in theater for a living—until he landed a record deal as a college freshman and went on to become the multi-platinum singer-songwriter you know today. Now, Groban is revisiting his first love on Stages (out now), a covers album featuring Broadway classics, iconic show tunes and duets with Kelly Clarkson, Audra McDonald and Chris Botti.

Groban talked to TIME about his song selection, his karaoke skills and why music needs more risk-taking.

TIME: You cover “Pure Imagination” from Willy Wonka & the Chocolate Factory—I didn’t know that had its own musical.

Josh Groban: It does now! It’s a bit of a cheat, one that I was willing to make because the song is so wonderful. It is on the West End right now, so technically, if we want to get lawyers involved, we didn’t break our rule.

But when will you cover the other great Willy Wonka classic, the Oompa Loompa song?

Oompity doo! Oh, yes. Well, Stages 2 will be all of the deep cuts, all of the under-appreciated songs. You never heard Judy Garland sing “Oompa Loompa,” and her loss, really.

Tell me about performing “All I Ask of You” with Kelly Clarkson, who is great but also not necessarily the first artist that comes to mind when I think Phantom of the Opera.

Right? That’s one of the things I loved about it. We all know she has a tremendous voice, but we also recognize that she takes risks, which I love about her. One of the things that has taken her outside of the Idol pack to a certain degree is she is her own artist, she is her own person, she is stubborn in her artistic convictions. I’ve always wanted to sing with her, and I’ve always thought she was a cool and funny person, so I’m thrilled that she jumped to it and immediately started singing the crap out of it. I’m so glad that our duet I’ve wanted was the first song I ever sang to get myself a record deal.

When I spoke to Kelly earlier this year, she talked about working on a country album and the possibility of doing a Broadway album or an R&B album. Do you feel the same freedom with your career?

Absolutely. There needs to be more risk-taking out there. I think that things like Twitter and the blogosphere are so instantaneously critical that I think it’s actually created a bit of a culture of artistic fear to branch out too much because you don’t want to be slammed. It’s great if you’ve got an instrument then can do all things, then go for it! Try different things! I don’t usually think of it in terms of it “Maybe I’ll go country next” or “Maybe I’ll go R&B next”—I try to use some of those influences when I can within the record.

You could probably break the Internet with album of ’90s R&B slow-jams.

I definitely break karaoke when my friends have birthday parties. I’m not going to say that when I sing R&B slow-jam ’90s songs we get free nachos, but I’m not going to say we don’t get free nachos. It’s pretty magical.