Michael Christmas wasn’t always smiling. The 20-year-old Boston rapper lived a sheltered life, opting to watch cartoons at home instead of run in the streets. But ever since he dropped the song/video “Daily” last year, his rap career started taking off. He’s gotten co-signs from JoJo and Childish Gambino and attention from outlets like Complex, Fader, and XXL.

Christmas is finding success by blending laughs with a love for all that defines him. He recently landed on our list of 25 Rappers to Watch Out For, but his music sounds like none of the other inclusions. The pop culture lexicon laces his songs, his favorite Pokemon is Zapdos, and he abhors the Nick Jr. show Little Bill.

Christmas, a.k.a. Bob Hanukkah, is just starting out, but if you ask us, it’s only a matter of time until he hits his stride and finds the right audience. That’s why we caught up with Christmas to discuss his childhood, a chance encounter with Childish Gambino, and his debut project, Is This Art?. Everything’s good, and it’s only getting better.

Interview by Alex Siber (@Alex_Siber)

You were raised in Roxbury, a neighborhood of Boston. What defined your upbringing?
I grew up on Warren Street, which for Boston is synonymous with shooting people. But I'm super not hood. I was always in the house watching Nickelodeon and playing with Batman action figures all day. Just imagine a small, short-haired me being uncomfortable around everybody. I knew what my neighborhood was like, and I was sheltered as hell because of it, so I just watched cartoons.

What was high school like for you?
I went to a private high school called Trinity, and it was super turnt. I got kicked out for not being able to pay tuition and ended up going to Charlestown High School, where I became really quiet because they just didn’t get me at all. I’d sit by myself at lunch and watch Adventure Time on my laptop.

I was supposed to graduate in 2013. I went to this alternative school my junior year. You come to school every fucking day to graduate faster. They said I’d graduate on time. In December of 2012, I came to class and they handed out this paper that tells you when you’re projected to graduate. It said, “March 2014.” I thought they made a mistake. I was happy as shit texting people like, “Yo, I’m graduating in March [of 2013]!” Then I called the teacher over to make sure, and he said, “Naw, this means March of 2014.”

I put the paper down, stood up, and immediately left. Didn’t say anything to anybody. I never came back to the school. I spent the first four months of 2013 moping around. Finally, I started making more music and made “Daily” in May or June of 2013.

I told my mom I was going to be a rapper. She basically said, 'Don’t smoke, don’t drink, don’t fuck white women, and you’ll be successful.'

For all the awkwardness in “Daily,” you also show a lot of charisma.
I get it all from my dad. I tell everybody my dad is exactly me if you took away the awkwardness and discomfort I always feel. We used to walk around together and he’d compliment girls as they walked by. I’d get mad because I thought it was embarrassing, but when I got older I thought it was hilarious so I started doing it. Girls get pissed when I compliment them, but I actually mean what I say. [Laughs.]

Describe the moment you were reunited with your dad.
My dad’s stay in jail felt like forever, for both of us. My favorite person on planet earth was kept away from me. I remember going to sleep early the night before just to wake up early to go get him. We pulled up, I got out of the car [knowing] he was out already. I look down the street and see him, he has these crinkly ass jeans on, this humongous white tee, and these white jail Chucks with no laces. He walks up with this big trash bag and I give him a big ass hug. It felt like he never left.

We bought him a big ass bottle of Hennessy and he was like, “We gotta go to Target to get the red cups.” [Laughs.] He was ready to turn up immediately. When we were in Target my sister just decided to lie on the floor. The first thing my dad did was lie on the floor with her. I actually have a picture of that. I appreciate every day he’s not in jail. I’m super proud of him and he’s super proud of me.

Your music from that time is much darker than Is This Art? You’re clearly in a different place now.
Absolutely. I don’t know where my life’s going, but it’s a different experience for me—people knowing who I am and respecting my work. During that time, my dad was still in jail and so many school issues brought me closer to that point of thinking, “I’m not gonna go here anymore.” I looked at the world like I hated it. Early in 2013, I started realizing it’s not that bad. There’s all this sadness but I’m still alive, I still have my homies, and my mom still loves me.

You released the reflective song “Self-Expression Interlude” last summer. Did something specific inspire that?
I think that day I might have also made “Michael Cera.” It was a one-take freestyle all the way through. The beat felt like sitting on a rug in a room full of tapestries with a hookah, and I don’t even fuck with hookah like that. Around that time we lost one of our homies, Von P. A lot of the inspiration for the song came from the day after he passed. We took a trip to gather ourselves and have a good time, we came back with this positive outlook.

That same summer, you went on a regional tour. How’d that impact you?
That tour with Cam Meekins and Shwayze came about the day before they left [for the tour], the day we finished “Daily.” I got a call from Tim [Larew] and he said, “You gotta come on this tour tomorrow.” I had a job interview the next day, and this was my second time scheduling an interview because I missed it the first time.

I could go to this job interview or tour the Midwest. I immediately was like, “Hell yeah, I’m going on this tour!” It helped me, being in new cities—Minnesota, Milwaukee, and Chicago—and seeing that somebody I know personally has fans helped me realize I can do this shit.

Later that year, your mom and dad came onstage for your first headlining show in Boston. What was that moment like?
That was the first time my moms actually saw me rap and it was with a sold-out, hometown crowd. She was pissed at my dad being drunk as fuck and dancing onstage, though. On my 18th birthday, I told her I was going to be a rapper. She basically said, "Don’t smoke, don’t drink, don’t fuck white women, and you’ll be successful." I did a lot of that shit she told me not to do, but I’m also trying to be successful too so I’m not a liar. [Laughs.]

If you met Michael Cera tomorrow, what would you say?
I’d introduce myself as Christmas because that’s my icebreaker right there. That’s how you get people to pay attention. I’d tell him, “Yo, so I don’t know if you’re mad, or if you saw it, but I made a song about you, and it did pretty well.” He’d hopefully ask to see it, then I’d show him, and we’d become best friends and watch TV and eat Bagel Bites.

I hear Childish Gambino showed you love for “Michael Cera” backstage at one of his concerts.
Backstage after his Boston show, Gambino stopped me. He’s like, “You’re a rapper, right?” I was like, “Yeah.” He was like, “What’s your name?” I was like, “Christmas, Michael Christmas.” He was like, “Word! I loved your video.” He loved “Michael Cera.” I was freaking out in my head.

We talked about unlubricated condoms. He said bras smell good. I told him if a bra gets thrown at me onstage, it might not smell good because the girls that are throwing bras at me probably don’t smell as good as his fans. [Laughs.] He told a story about how his dad gave him a condom for prom. He was like, “If my dad knew how long it actually took to get laid opposed to how long he thinks it took, he’d probably just die.” [Laughs.].

Childish Gambino told a story about how his dad gave him a condom for prom. He was like, 'If my dad knew how long it actually took to get laid opposed to how long he thinks it took, he’d probably just die.'

You have a lot of '90s throwback references on Is This Art?.
I don’t really believe in bringing the '90s back, I just believe in talking about the shit I loved growing up. If I go to my show and I play the Pokemon song and I see people who know it, I’m like, “You get where I’m coming from.” You know what I watched that’s underrated? That show Oswald about a big ass, friendly octopus and his friends. They have jobs, they roast marshmallows, they’re above water. They just happen to be octopuses and penguins and shit.

Same thing with “Broke & Young,” when I did the “15 bucks little man” [bridge], I got that from Jay & Silent Bob. When I opened for Bone Thugs, I started singing that. People knew it and it was so tight. It’s like when you’re talking to one kid about your favorite movie and another comes out like, “Yo! You fuck with that?” Then you just become friends. This is me becoming friends with everybody.

Some say the secret of life is not taking it too seriously. Would you say that’s been a recipe for your success?
Absolutely. You have to take some things seriously because if you don’t, you’ll be homeless. Taking things too seriously, you don’t give yourself a chance to realize that you only have one life. When it’s over, it’s just over. You don’t get to laugh about the things you wanted to laugh about.