The oral history of Drake’s I’m Upset music video, featuring the cast of Degrassi

The oral history of Drake's I'm Upset music video, featuring the cast of Degrassi
Photo courtesy of Pat Mastroianni

Back in June, cast members from Degrassi: The Next Generation heard from their old friend Drake (AKA Aubrey), who wanted to get the gang back together to film a music video for his new hit “I’m Upset.” The nostalgia-fuelled reunion has since been viewed more than 73 million times on YouTube and has given fans a good reason to re-watch Canada’s favourite high school drama. Toronto Life spoke with ex-Degrassi kids Jake Epstein (Craig), Shane Kippel (Spinner), Miriam McDonald (Emma), Stefan Brogren (Snake/Mr. Simpson) and Pat Mastroianni (Joey Jeremiah)—who will all be appearing at Fan Expo in Toronto on August 30—about the music video, young Drake and the beloved TV show. 

So a couple of months back, you’re going about life as usual and suddenly you find out you’re going to be in a Drake music video. What was that like?

Shane Kippel: I was out on a run when my phone rang. It was a friend who worked on publicity for Degrassi. He was like, “Shane, where are you? Are you sitting down?" And then he told me that Drake had this idea for this high school reunion video. At first, it seemed a little too cool to be true. But sure enough, two weeks later we made the video.

Miriam McDonald: By sheer coincidence, I was actually listening to Drake on my headphones when I got the email about doing the video. My response was yes, with seven exclamation points. I still see him as the guy I grew up with, but I’m also a big Drake fan. It’s kind of like there are two different people. Before the shoot Cassie Steele and I laughed about not knowing what to call him. Aubrey? Drake? 

Jake Epstein: We don’t know who Drake is. Aubrey kept turning to me all day saying, “Nothing’s changed, eh, Epstein?”

McDonald: He said to us, “Guys, this is your party, you can stay, you can leave whenever you want. And we were like—who do you think is going to go anywhere?"

What was the shoot like?

Kippel: It was three days in total. I was in the driving scenes with Aubrey, so it was cool that we got to hang out. And I got to keep the suit.


Epstein: I thought you were going to say you got to keep the car!

Brogren: I brought in my own suit because I wasn’t sure what they were going to give me for Mr. Simpson. They said, “No, you can’t wear that because it’s going to get ruined.” I didn’t know there was going to be spray painting.

Kippel: And that Shane might puke on you.

Brogren: Right. I was actually on set when I found out this was going to happen. Iain Christensen, who worked on Degrassi with all of us, asked if I wanted to smoke weed in a Drake video with Kevin Smith and Jason Mewes. I was like, of course! That weed was absolutely fake, but it was definitely a party on set. There were lots of bars set up, and lots of expensive champagne.

McDonald: Definitely a lot of alcohol...


Epstein: We’d be hanging and dancing and then we’d realize the camera was on us.

Brogren: They brought in a DJ from LA who was playing music through the whole thing because hey really wanted to keep the party vibe going.

Kippel: And then the whole OVO crew was in the back hanging out with a bunch of models just watching the whole thing happen.

McDonald: There were a little bit intimidating. There was a whole wall of them.

Who wants to take a crack at explaining the plot of the video?


McDonald: I feel like it centres around the friendship between Spinner and Jimmy.

Kippel: The idea is that it was supposed to be the day after the Raptors lost. That’s why Drake wakes up in the ACC. The cool thing was that he was Drake in the video, but he was also Jimmy. So there’s this illusion that we’ve all been hanging out since high school and then end up crashing the high school reunion.

Epstein: It was a really cool thing for him to pay homage to this time in his life and not forget where he comes from. One of my favourite parts is the cameo by Ephraim Ellis, who played Rick, the character who shot Jimmy during the high school shooting episode. In the video Jimmy and his boys went after him. It was like this awesome moment of retaliation.

Brogren: It was half us having fun as our old characters and half having a genuine reunion. 

Snake—if I may call you Snake—were you worried about exposing Mr. Simpson as a stoner?


Brogren: I would have done anything they asked me to do. In the original rundown, Snake was supposed to hang out with strippers. Part of me was nervous about having Lynda Schuyler, who created the show, see Mr. Simpson smoking weed, but it wouldn’t be Degrassi if people weren’t screwing up. So what? Simpson likes the chronic—is it even called chronic anymore?

Kippel: No.

Who was the nude guy in the video?

Kippel: He was a guy from the crew. We had timed exits at the end, and I ran right into him. That wasn’t on purpose.

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Pat Mastroianni: Absolutely he does! I’m not sure why we’re not opening for him. I didn’t appear in the video because it was a tribute to his generation of the show. Stefan is a great ambassador for all of the different generations. I was just proud of my friend.

Brogren: And I was like, how am I going to tell Pat?

Who doesn’t want Joey freaking Jeremiah at their Degrassi reunion?

Where’s the fedora?


Mastroianni: It’s at home.

Stefan: I think it has to be at Fan Expo. These expos are so cool. You’ll have a 13-year-old  come up to you, and you have no idea which Brogren they’re going to want to talk about.

Why do you think Degrassi continues to resonate with fans all these years later?

Brogren: I think the producers were very smart to cast age appropriate actors so kids weren’t watching a 22-year-old playing a 13-year-old having sex for the first time.

Mastroianni: There was a mandate for the show: never have an adult answer a question. A character would make a decision and there would be consequences, but it was never about going to the guidance counsellor and saying, “please help me with this problem.”


Epstein: When we were shooting Degrassi: The Next Generation, we would have these table reads and the producer would always ask, “What’s going on, what’s stressing you out right now?"

Kippel: The writers were in their mid-30s and they’d ask about the language. “Would your characters say this? Do kids even talk like this anymore?"

McDonald: We would be in the lunchroom and the writers would casually walk up and ask to join us. I’m pretty sure they were spying on us.

Epstein: Totally. It was very casual like, “So how do you guys feel about abortion?”

When you look back at Aubrey during those years, did you see signs of future greatness?


Kippel: He was always a captivating guy. He would always be the centre of attention, but not because he was trying to be.

Brogren: The crap that came out of his mouth was always hilarious. That’s why I was so excited when he did Saturday Night Live, so people could see how funny he is.

Epstein: And he was always really driven. In between scenes he’d go off and be writing lyrics and one year, he came back from the break and was working with Pharrell. We were all like, “Okay, you’re legit.”

Are any of you guys still in touch? Like, could you text him?

Kippel: I don’t know if I would text him, but I’m probably the one who is most in touch. We message each other on social media every couple of months, but before the video I probably hadn’t seen him in five years.


Do any of you ever get free Raptors tickets?

Everyone: No!

Kippel: We’ve got to work on that.


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