Rapper Michael Christmas to Headline Lemur Fest at the Grog Shop

“I want to be like Shaq,” Michael Christmas says in a recent phone interview, speaking about the former basketball star’s seeming omnipresence across media and pop culture, “He’s even DJing now! I’m not saying I’m going to be a DJ… But I’m not gonna say I’m not gonna be a DJ.”

The 23-year-old has multi-platform hopes for his future, but on July 22, he’ll make his first trip to Cleveland to headline the Grog Shop’s third annual Lemur Fest. Christmas is excited to come to the city; he’s a fan of King Chip (aka Chip Tha Ripper) and Bone Thugs N Harmony, and notes the influence of Kid Cudi on internet kids of the late 2000s.

“Cudi made the Cleveland C hat look so fucking cool,” he notes, “I had a friend in high school who used to wear the Kid CuDi starter kit: tiny ass pants, tiny ass Nike hoodie, and the Cleveland C hat with the crazy bent brim. Cudi made the brim so much more bent and I was like, ‘That shit is lit.’ And I was all over that — I was always on the internet because I didn't have friends.”

The Boston rapper has made a name for himself with reflective, poignant, smoked-out raps that, like his comment above, toe the line between hilarity and sadness, a line that Christmas has walked since childhood. Instead of peers, he was surrounded by pop culture, growing up with a slightly too early introduction to provocative critical darlings of his stepfather’s canon — Biggie, Dave Chappelle stand-up sets, NWA, Eminem, Spike Lee.

“I got picked up from school and was immediately immersed in adult shit,” he says. “I remember thinking some was really dark, weird stuff that made me uncomfortable [Eminem’s ‘Go To Sleep,’ Biggie’s ‘Who Shot Ya?’], other stuff I would start to bump myself and absorb. Ice Cube became my favorite rapper pretty quickly.”

He credits both those musical influences and his days spent skipping school to watch television for his music’s robust imagery and word bank. Bumping around schools and finding it tough to make new friends, he spent a ton of time pretending he was sick and watching cable in his mom’s room, guzzling movies and TV. In seventh grade, he found his own outlet through music, downloading beats from the internet or YouTube and making his own songs. After a few unlucky financial circumstances that led to being kicked out of a private high school, that outlet that quickly became his Plan A.

A series of chance encounters late in high school were key to kickstarting his career. He ran into a former camp counselor who ran a streetwear store on Boston’s Newbury Street, a trendy shopping district in downtown Boston.

“I was 15, 16, broke as fuck, trying to get my shit together, and just told him, ‘Yo, let me work here. Whatever I need to do, I’ll do,’” Christmas recalls. The friend gave him an internship, a position that opened the young rapper up to his community. He’d play his own music on the speakers and rap for anyone who asked about it. He had a stage before he had a stage.

Musically, Christmas’s main crew also had an odd genesis. Back in 2012, he got sick right before A$AP Rocky’s first Boston show. After trying to sell the ticket on Twitter, a young rapper named OG Swaggerdick said he’d buy the ticket off him for $25.

“I gave him the address and told him, ‘Bring money.’ He didn’t bring any money!” Christmas exclaims, “He brought a pair of sneakers, saying, ‘Hold onto these until next week, and I’ll bring you the money.’ He brought me collateral! I’d never gotten collateral before.”

OG stuck to his word and came back to pay the next week. The pair started chatting, talking about music, and sending each other beats. Eventually, they decided to make a song together, and when Christmas took the bus across town to meet up, OG was with two other kids, Ian Goodwin and Tim Larew.

“I did the verse, they started fucking with me, and I was down with them,” Christmas remembers. “I’d found people who were thinking on the same wavelength as me and just said, ‘I wanna be around y’all all the time.’”

Goodwin has become Boston’s hip-hop jack-of-all-trades, taking photos, DJing shows and directing videos for a number of the city’s emerging artists. Larew was a Boston University student whose blog, Fresh Heir, became a pivotal platform for connecting and networking the local scene. Larew now manages a number of those artists he helped promote, including Christmas and Cousin Stizz, the city’s underground prince.

Along with their musical influence, these first real friends got him out of his personal rut. “I didn’t really have anything, so they pushed me to get my shit together and also have more fun,” he says, “I was really depressed for a long time, but hanging with them, I made myself get up every day and go. Those were the best moments — even if it’s baby steps, I was progressing.”

These four kids have become pillars of a flourishing upstart Boston scene, producing the city’s first nationally recognized hip-hop artists in almost twenty years. Though a major metropolitan area, Boston arguably hasn’t had a true rap star since Gang Starr in the '80s and '90s. Through Stizz and Christmas’s trailblazing, the rest of the scene has followed — Big Leano, OG Swaggerdick, Haasan Barclay, and Vintage Lee have developed a palpable buzz in their wake.

“This whole thing is Marvel — we started out with just Spiderman, and then we’ve got the Avengers, and now we’ve got Guardians of the Galaxy and Ant Man,” he says, whipping out film references. “There are these super talented people popping up that no one knew was here. We needed to believe in ourselves, and now the city will support the shit out of you.”

Christmas has led with his music in a tremendously refreshing way; he’s an awkward kid who can just lay bars, his lyrics spiraling around observational humor and self-deprecating shrugs, all packed with pop culture references. He raps about hot pockets, being alone, and Bedazzled in “Daily” (“After that I ate it/and that shit was the greatest/and then I masturbated/I felt like Brendan Fraser”) and makes Superbad and Arrested Development metaphors throughout his breakout hit, “Michael Cera.”

He’s cited Los Angelino Dom Kennedy as an influence, one you can see in his laid-back delivery, smoky production, and knack for narrative. It all comes through a natural, head-nodding cadence that feels simultaneously pedestrian and polished, perhaps owing to a fast, instinctive writing style. He can bust out a feature verse in ten minutes (“No exaggeration,” he says), and often procrastinates until he’s on the way to booked studio time or in the booth itself to write his lyrics.

Christmas’s stylish, goofy, rumbling sound has garnered him plenty of attention. His 2015 mixtape What A Weird Day launched him into the national limelight, a diverse offering that landed him on national tours with Mac Miller and Logic. He got tapped by the mysterious, critically acclaimed producer Prefuse73 for a collaborative album last year, and recently co-headlined dates across the country with emerging west coast acts Warm Brew and Boogie.

Christmas is soaking it all in. From where he was just a few years ago — inhaling daytime cable in immovable depression — he is both appreciative and in awe of the experiences he’s afforded today. He tells wide-eyed stories about going backstage at an FKA Twigs show and it resembling a 1980s art gallery while he was just wearing swim trunks and a T-shirt, or daring OG Swaggerdick to take over the aux cord at mansion party in the hills of Los Angeles until they almost got kicked out.

He’s started semi-jokingly putting Moët on his backstage rider, but still steals the food from the dressing room. At a recent festival, he found himself being hurried out of his trailer, walking around the artist village with his iconic princess backpack stuffed with champagne and snacks, carrying a Costco-sized bucket of cheese puffs.

It’s a good reflection of where he finds himself today: still awkward, garnering deserved recognition, happy to be here, and moving towards the future, cheese doodles in hand.

Lemur Fest 3 featuring Michael Christmas, Joey Aich, Dom Deshawn, Bobby Booshay, DJ Cooley High, Latchkey, MELLOW-XZACKT and Kent Archie, 8 p.m. Saturday, July 22, Grog Shop, 2785 Euclid Heights Blvd., Cleveland Heights, 216-321-5588. Tickets: $10 ADV, $15 DOS, grogshop.gs