An MC since the age of 16, Toronto rapper D-Sisive (government name: Derek Christoff) made a name for himself thanks to his clever, whimsical punchlines and a gag-filled live show. Despite releasing spurts of music each year, as well as touring the UK in 2005 with Abdominal and DJ Format, it took some time for him to release his debut LP, The Book. Now that it’s out, a marked difference is visible — whereas previously, humour and a low-key swagger were his calling cards, The Book is marked by introspection and melancholy. It also begins with a Daniel Johnston cover, acknowledges the plight of the white rapper and, surprisingly, contains a cleared Tom Waits sample. Suffice it to say, it’s a unique and concise work. Over some pork and rice, D-Sisive discusses his new release.

How did you wind up getting the Tom Waits sample on your song “Underground” cleared?
I did it like “Nightclubbing” [an unsanctioned single sampling the Iggy Pop song of the same name], and put it on the internet. I had friends in bands who said, “I don’t know, Tom Waits is really rough about copyright stuff.” But my manager was in contact with his manager. He sent the song, and fuckin’ two days later I get an email saying “Tom really likes the song, here’s the clearance.”

He even let you use the chorus.
Believe it, it shocked me as much as anything else. It goes to show he’s probably a nice dude and down-to-earth, [even though] I hear all these horror stories about him suing everybody. He has tracks, man. “Underground” wasn’t even my first choice.

He’s like Timbaland.
He’s the Timbaland of stick bass and jugs. 

Speaking of musicians, you told me earlier Raine Maida was an inspiration for you.
Yeah, on [Maida’s solo album] The Hunters Lullabye, he’s rapping on it. I remember reading an interview with him where he said, “We’ve got a lot of hip-hop influence on this record.” You don’t! There’s no hip-hop influence on the Raine Maida album! It’s spoken word. He says stuff like “Leonard Cohen on a camel” — you can’t say that on a hip-hop record!  

I reviewed it.
What did you rate his record?

Two stars.
Why not one? Is the extra star because he busks? I remember seeing him busking on Queen Street for his video shoot. He was rapping, and I remember thinking, “This is really weird. This guy is taking my spot. I can’t let that go.” So I made my album. Raine Maida woke me up.

Your lyrics deal with the insecurity you felt as an artist. Are rappers insecure?
I think so. It’s also perfectionism. When you start making music, you have this dream of success. When it started to happen at all for me, it started feeling uncomfortable, and I felt overwhelmed by it all. I wrote one song [“Whatever Happened to the Music”] that everybody loved, that got me my management deal in LA, but I still needed four, five more. Then it put this crazy pressure on me. There was a point where I was getting paid and I wasn’t delivering music. Every song I wrote, I was, like, “This is not good enough.” Then you start asking yourself, “What is good enough?” But now I feel like a new artist. I’m back on my grizzly.