Boston Rapper Michael Christmas Grows More Popular And More Personal On His New Album

On a Friday afternoon in October the Roxbury rapper Michael Christmas rolls up to his favorite Boston haunt, the hipper-than-hip sneaker shop Bodega. It is one of the first cold days of the season, and Christmas wears his puffy afro squashed beneath a baseball cap and a hoodie, enhancing the impression that he is as much a soft, huggable stuffed animal as a man.

"I’m hideous," he says at one point during our conversation. "But also cute."

That pretty much sums up the 21-year-old rapper’s persona — simultaneously self-deprecating and pleased with himself. Christmas, whose given name is Michael Lindsey, is promoting his sophomore album, “What A Weird Day.” He celebrates its release with a show at the Middle East Downstairs on Monday, Nov. 9.

“What A Weird Day” is the follow-up to 2014’s “Is This Art?,” the jokey, pop-culture-reference-packed debut that piqued the interest of hip-hop-heads beyond just Boston and earned the young rapper a feature in indie-cool arbiter The Fader and a spot on Complex magazine’s list of “25 New Rappers to Watch Out For In 2014.”

“What this album is is you take the weirdo rap kid artist regular guy loner, and you put him in front of a huge spotlight,” says Christmas. “And you give him all these things that he’s never had and never dreamed of having, and the album is how I feel about that. It’s like, OK, now I’m playing these huge shows. I was getting beat up [before]. ... These are all things I never dreamed would happen and that’s what’s happening. So what I’m kind of telling people is, you, as the weird kid, and the loner, can do the same thing.”

For “What A Weird Day,” Christmas decamped to Los Angeles, where he rented an apartment and wrote new songs. Most of the tracks on “What A Weird Day” are produced by non-Bostonians — the LA-based Polyester the Saint, the Canadian Rich Kidd and the Chicago native Thelonious Martin, to name a few — although the album does feature contributions from the Boston-based Teddy Roxpin and Qreamybeats.

The lead single off of “Is This Art?” was “Michael Cera,” a pun-packed riff on the “Superbad” actor whose success playing bumbling characters is something Christmas emulates in his own work.

“What A Weird Day” contains a more serious bent. “I didn’t rap about girls much before,” says Christmas. “I was just like kinda scared to do it. And I also didn’t really have too much to say.” “What A Weird Day” contains two love songs, both somewhat unrequited. “I Wrote A Poem,” says Christmas, is about the girl he pined for last year, while “Perspective II” is about the one he likes now. “Up in space, it’s me and you/ A couple brews/ I’m still trying to see if they got free Wi-Fi on the moon,” he jokes in “Perspective II,” all charm and vulnerability, over a wistful flute sample that’s as ethereal as love itself.

“What A Weird Day” also references Christmas’ childhood more earnestly than before. On “Think You Grown,” he raps about the bittersweetness of chasing a career, which takes him away from his family: “I work too much/ I sleep too long/ My mama keep calling me/ She scared when I’m gone.”

“My mom and my dad broke up when I was born, basically. And there were points where my mom was kind of supporting me on her own,” says Christmas. “There were points where she would lose a job or something like that and we would have to go stay at other people’s houses. Mind you, I didn’t know that these were other people’s houses. I always thought it was my house. I didn’t know we were homeless.”

Christmas’ mother is a constant presence on “What A Weird Day,” calling him, chastising him, looking out for him. But he has an even closer relationship with his dad. Christmas says he dropped out of high school right around the time his father started a stint in prison (he has since gotten out), which the rapper remembers as one of the toughest periods in his own life. But he also says hardship is how his sense of humor took shape. “Dark humor is me and my dad. We think the worst s--- is funny. But it’s like, you have to laugh at those things.”

“He says all his friends ask him how he got his son to love him,” says Christmas, “and he’s like, be a dad. Like, it’s not that hard. Don’t look at your kid as an enemy, look at your kid as another human being that you have to build up to be cool and smart and responsible. And he made me cool and smart.”

On “What A Weird Day,” Christmas cultivates a gleeful, yet disbelieving, tone in response to his newfound indie celebrity. He says he still finds it disconcerting when people recognize him on the street — he’s accustomed to being invisible. I ask him if he used to feel more invisible than everyone else.

“A little more invisible than a regular person,” he says. “A regular person has their group of friends that they’re used to, so they’re not invisible to them. Up until I was probably 17 or 18, I didn’t even have that. I switched schools so much and moved around Boston, even though I stayed in the same general area of Roxbury. I never went to the same schools and I never hung out outside of school. So I didn’t have friends outside of school. Or, really, in school.”

Despite his growing popularity, Christmas recognizes, rightly, that his outsiderness is the key to his success.

“2015 is a time where everybody is kind of being more accepting,” says Christmas. “You see on Instagram and Twitter, these girls that are very body-positive. And that’s awesome. I love that. Girls are just naked all the time. That’s tight. And it’s beautiful, it’s a beautiful thing.”

He continues: “The nerds are the cool rappers now and dressing weird and bummy is the thing to do. And I feel like I was ahead of the curve with that. Because when I came out, everybody was calling me the regular guy rapper. And now it kind of feels like everybody is trying to be more relatable. Which is a good thing. That’s better for music, that’s better for people.”