Shalom Life | July 10, 2015

Breakthrough Jew: OB O'Brien

The recent signee to Drake's OVO label is looking to put Hamilton on the rap

By: Sara Torvik

Published: December 18th, 2014 in Culture » Music » News

Hot, hip, and heady, the next wave of Jewish artists and influencers has already arrived. This is Breakthrough Jew, your weekly showcase of those on the verge of discovery and ready to be a regular figure in pop culture; setting trends, redefining genres, and simply getting it done-whatever ‘it’ is. These days, it’s not enough to know what’s hot now; you need to catch someone when they’re just starting to simmer.

Featuring those in film, fashion, food, and beyond, we’ll find the story before substance is obscured by style, before hype meets backlash, and before talent and purpose gets lost in a maze of Internet chatter. See an artist in the cozy bar before they hit the amphitheater, dine at a chef’s new restaurant before the line begins, and catch a young writer’s work before the demands of ratings and longevity encroach.

Follow our lead and we’ll follow yours – send us tips or suggestions via email, comment below or tweet us @ShalomLife, as we explore the Jewish landscape for pop culture pioneers.


Name: Matthew “OB” O’Brien

Age: 30

Hometown: Hamilton

Breakthrough Cred: Collaborating with Drake

You might not know too much about Hamilton rapper OB O’Brien but if you’ve seen any of Drake’s music videos you probably would know his face right away. The now 30-year-old O’Brien got his start appearing as Drake’s “sidekick” in a number of his videos and TV appearances, but now it seems he is branching out and creating a name for himself. His new single “Schemin’ Up,” (with fellow OVO signee P. Reign) which is being released on Drake’s OVO label, has been getting a lot of exposure on major music sites lately, and Drake naturally makes an appearance on the track as well.


So who is OB O’Brien, really? And how did he become a significant part of Drake’s in-crowd? As it turns out, he actually comes from a very musically accomplished family. His father is Michael O'Brien, who was a Hamilton Music Award-winning bluesman (who passed in 2010). And 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. O’Brien grew up with music in his blood so it’s no surprise that he took that road, too.

As a teenager, O’Brien attended Westdale Secondary in Hamilton, where he'd host and perform skits at pep rallies. He also studied at Humber College's Comedy Writing and Performance program. All through high school and college, O’Brien was slowly building a name for himself by rapping and producing beats. It was through all this that he was introduced to Drake (then Aubrey Graham) sometime near the end of his run as the wheelchair-bounded character Jimmy Brooks on Degrassi. The two hit it off and became instant friends. After Degrassi, Drake was involved in the production of an independent television pilot and he asked O’Brien to be a part of it, saying, “No lines to memorize, just come and improv.”

And that’s how it all got started.

But beyond being Drake’s right-hand man, O’Brien has always tried to maintain his own identity and continue to create his own music. He has released a few tracks so far including the aforementioned “Schemin’ Up,” and also, “Steve Nash,” and “2 On Thotful” (a remix of Tinashe's "2 On"). He has also appeared as a guest on tracks by other well-known Canadian rappers, such as “Say It” by Toronto hip hop artist Saukrates. Toronto producer Boi-1da, who has worked with well-known artists such as Nas, Kanye West, Eminem and Nicki Minaj, also produced and previewed O’Brien’s upcoming release entitled “Jewish’ at The Red Bull Music Academy’s showcase Drum Majors last year.

There’s no word yet on an official release for O’Brien’s upcoming LP for OVO, but we are looking forward to hearing it. And in the meantime, anyone who wants to hear the track’s he has already released can do so by checking out his Soundcloud page.

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