Who is that wisecracking Hamilton beardo in all of Drake’s videos? Meet OB O’Brien

wisecracking Hamilton beardob

A little investigation into Drake mascot and Hamilton rapper/ producer OB O’Brien

Jordan Darville’s interview with Jessy Lanza got the Chart Attack office thinking about Hamilton, the cheaper, friendlier idyll, an hour south of Toronto. And so when Drake released his latest blog-igniting video, it was only a hop, skip, and a jump before someone asked, “Who is that bearded white dude in all of those Drake videos, repping Hamilton every here and there.” (Okay nobody said that verbatim, but that’s the gist).

He’s there in the “HYFR” video. There he is again as Drake’s gameless co-worker in “Started From the Bottom” (though that “Oh my Bosh” is worth a giggle). He was at Drizzy’s side when he gave a shout out to Hamilton at the 2012 VMAs. And now, he’s turned up again, this time in OVO owl suit for “Worst Behaviour,” trying to pass mixtapes off on Juicy J and Project Pat of Three 6 Mafia.

Who is this wise-cracking beardo, who’s got two fistfuls of Drake’s coattails? As Chart’s resident “Hamilton guy,” the investigation got thrown on my pile. Here’s the dossier I’ve compiled on Hamilton’s OB O’Brien.

Matthew “OB” O’Brien, 29, lives and grew up in Westdale, Hamilton’s quaint, tree-lined, university neighbourhood. His dad, Michael O’Brien, was a Hamilton Music Award-winning bluesman (who passed in 2010). His brother, Jesse O’Brien, is an accomplished keyboardist who’s shared the stage with Levon Helm, Harrison Kennedy of soul legends The Chairmen of the Board, and Junkhouse’s Tom Wilson. So, yeah, music runs in the family.

wisecracking Hamilton beardo

O’Brien attended Westdale Secondary, where he’d host and perform skits at pep rallies. He did Humber College’s Comedy Writing and Performance program, which kind of explains the Drake’s funnyman sidekick stuff. Through high school and college, OB rapped and produced beats. Through that kind of gaming he was introduced to a young Aubrey Graham (that’s the name on Drake’s license) sometime near the end of his run as Jimmy Brooks on Degrassi. And the two kind of hit it off. After Degrassi, Graham was involved in the production of an independent television pilot and he tapped on his new, spontaneous, wisecracking friend, O’Brien, to join the project, promising, “No lines to memorize, just come and improv.” Who knows what came of the show, but that’s where their relationship starts.

Beyond appearing as Drake’s court jester, OB’s been trying to break his name as an artist in his own right. Here’s a forgettable verse on a jam by Toronto hip-hop icon Saukrates, though I’m sure one of the first to name-check both Don Cherry and Habs defenceman P.K. Subban in song.

And OB’s been calling on heavyweights to help on his debut mixtape. Toronto superproducer Boi-1da, whose credits include songs for Nas, Kanye, Eminem, Nicki Minaj, Talib Kweli, and of course, Drizzy himself, recently previewed this snippet at The Red Bull Music Academy’s hitmaker showcase “Drum Majors 2013.” While Drake may have made a boozy re-Bar Mitvah into a music video, he’s stopped short of emphatically shouting “Jewish” as a hook in itself. Not OB, he just went for it.

And here’s a clip of OB with Ajax’s T-minus, who’s worked with A$AP Rocky, Lil Wayne, The Weeknd, and Kendrick (credit on the basically career-making — as far as radio and club play goes — “Swimming Pools”) to name a few. For all of the star power in tow, there’s still no word of when OB’s debut will drop. But he’s a busy guy. He’s tried to keep his hands in the production side, too. According to this, now a year old, he’d just finished a song for Rihanna.

Lastly, I haven’t been able to parse this TOPSZN shit that OB keeps trying to make happen. Apparently, “TOPSZN is the regime.” Look into it and that’s about all you’ll hear. It certainly appears on a bunch of shirts and toques and shit. Maybe it’s some upcoming affiliate to Drake’s label, October’s Very Own. Or some cute little club with Champagne Papi tag-along #2 OVO Ryan. It seems to be a strain of medicinal weed. But this case isn’t closed just yet.