To DeMar, From Toronto: A Goodbye Playlist for DeRozan

23 songs to say goodbye.

There are a lot of ways to say goodbye. There’s the quiet farewell, the heart-rending, really prolonged exit, a cold sendoff, the firm hasta la vista and an open-ended, optimistic ’til next time, just to name a few. Turns out there’s even more ways to say goodbye to a beloved athlete.

While the dust around DeMar DeRozan’s departure from Toronto has mostly settled, there are still whirlwinds stirred up here and there and likely will be all summer, probably all season. Regardless of how you felt about it—are still feeling abut it—the bottom line is you felt something. DeRozan was drafted to the Raptors and was the longest standing player the comparatively young franchise has ever had. In many ways, and it’s clearer every year and through each iteration of the team, Toronto suffers from growing pains. Like the city the team represents, its identity is a heavily nuanced, emotional and tricky thing. DeRozan embodied it and, like the city he called his second home, went through a multitude of roles in his time here. Going from a rookie, to infamously claiming the mantle of responsibility (and expectations of a city) in a rebuild, to a natural leader in the most successful stretch of seasons the team had ever seen, DeMar DeRoZan stepped into each role with the confidence and quiet assurance of someone who understands the full weight of what they are moving toward, because they have done the work to get there.

DeRozan grew with the team, but he also grew the team, the franchise, the city itself. The optics around the Raptors swelled when his success did. The accompanying confidence felt by fans and Torontonians fed back into the city and it is not a stretch to lay some of the boom in Toronto’s economic, social and cultural clout, if not its outright physical development, on DeRozan’s shoulders. Basketball is a business, after all. That’s why it’s only natural for the feelings surrounding his departure to be just as nuanced as his time here. A player like DeMar DeRozan doesn’t just up and leave a team overnight when traded. There are going to be tremors felt in all the parts of the city and country, beyond basketball, he touched.

I will be honest, the idea for this playlist was a selfish one. I meant for it to be a cathartic exercise to make up for not being able to wrangle, let alone put into words my own feelings around DeRozan’s departure. The idea was that in gathering up one song that summed up DeRozan from Toronto people who wrote about him for a living, were artists and feral fans, or else saw him as a part of the city they came from, the music could do the talking. It would soothe a little bit of the ache or abruptness in his absence. It didn’t do any of that. Instead it just piled on a hundredfold that one basketball player had become so many things, to so many people, in a city that was lucky enough to hold him for so long.

Jack Armstrong, Sportscaster

‘Winners’ – Frank Sinatra

Though he didn’t win a Championship here in Toronto, in my eyes he was a Champion in how he carried himself as a Professional Athlete, Sportsman and much more importantly as a True Gentleman. A class act who gave everything he had each day. To me that makes him a Winner and Champion in my book. In my 20 Seasons with the Raptors he’s definitely been one of my all time favorite players and people. A top shelf individual.


Seerat Sohi, Writer, SB Nation

‘Straight Outta Compton’ – N.W.A. and ‘Know Yourself’ – Drake

Last year, I was sitting in the press row and noticed something: the sound operations people changed the song that played when DeRozan scored from ‘Straight Outta Compton’—self-explanatory—to ‘Know Yourself’, the part that goes “I was runnin’ through the six.” I actually never asked DeRozan about it specifically, but I have asked him about branding before, and he said he’s usually into marketing that feels authentic to him. I don’t know if it was his idea, or if somebody brought him the idea, but the shift fit incredibly well with the guy who came to wear two cities on his back, who announced on a podium, “I am Toronto” after signing his third, longest-term contract with the Raptors. As much as the fanbase grew with DeRozan in what’s been the most exciting time ever to be a Raptors fan (and maybe a Torontonian, but who knows, I haven’t been here long) he grew with them too. Eventually, he considered Toronto home. Things are obviously raw right now, but I hope he always does.


James Herbert, Writer, CBS Sports

‘Compromise’ – Shad

I’m picking ‘Compromise’ by Shad, and it’s not just because he references Rafael Araujo and the Raptors’ then-abysmal draft history in the first verse. (This song came out in 2007.) It’s because Shad touches on self-improvement and—as you might have guessed from the title—a refusal to compromise who you are. And, yeah, the fact that this is a Canadian artist who is proud of that fact and name-dropped DeMar on a Drake dub a few years ago doesn’t hurt, I guess. 

Anyway, one of the things I appreciated most about DeMar’s time in Toronto was his insistence on staying true to who he is. He read all the criticism of his game and, rather than becoming a different type of player, he just kept tinkering, watching film and becoming a better version of himself year after year. As a result, DeMar has few stylistic peers in today’s NBA. 

When I interviewed DeMar six months ago, I asked him about the reaction to him shooting more 3-pointers this past season. He said he was kind of sick of talking about it as if it was a massive change. DeMar acknowledged that he had to let go of his need to prove people wrong, but he insisted that his shift was on his terms, not anybody else’s. He never intended to go his whole carer avoiding 3s, he just didn’t want to force it.

One quote that didn’t make the story: “You don’t want to be like everybody else. You just want to be yourself. I never compromised myself for nobody else. If it’s accepted, great. If it’s not, I’ma stand up for whatever I believe in and keep fighting for what I believe in.”


J.E. Skeets, The Starters

Por Ti Volaré’ – Andrea Bocelli

DeMar DeRozan and Kyle Lowry were sports’ greatest bromance. They won a bunch of games together, lost to LeBron together, and roasted each other constantly. They were more than best friends; they were brothers. “Step Brothers”? Sure. You thinking of the Catalina Wine Mixer scene? You know it. Is DeMar more of a Brennan or a Dale? Doesn’t really matter. Prestige Worldwide!


Tas Melas, The Starters

‘Because You Loved Me’ – Celine Dion

You were my strength when I was weak
You were my voice when I couldn’t speak
You were my eyes when I couldn’t see
You saw the best there was in me
Lifted me up when I couldn’t reach
You gave me faith ’cause you believed
I’m everything I am
Because you loved me


Kate Ziegler, Actor

‘Because You Loved Me’ – Celine Dion

I think about this song when I think about DeMar because he always fought for this team and our city with the tenacity of a son, a brother, a dad, a man who loved what he did and the people he did it with and for. So many times, the look in DeMar’s eye gave me the faith that our team was ready for a fight, I’d see in him the raw ambition to succeed and because he did we did. All that DeMar promised to this city, all that he delivered, what he shared about his heart and family struggles – the more we knew about him the more special his loyalty became. The laughter he and Kyle shared, the best friendship always made me feel like this was more than a team for DeMar but a family. I will never not be rooting for you DeMar because you are the most beautiful human, not for what you do but how you do it. Raptor claws up you god damn angel. And have fun in San Antonio you deserve every second of glory that comes your way. 


Rollie Pemberton, Musician (Cadence Weapon), Poet

‘Loyalty’ – Kendrick Lamar ft. Rihanna

I went to my pickup basketball game on the day of the transaction in Regent Park and we couldn’t even really talk about it. How could they trade DeMar? I’ve lived and died with the ups and downs of this team since their inception and DeMar has ever since he was drafted by the Raptors in 2009. He’s had several opportunities to bail, to pout, to demand a trade and throw the team under the bus but he never did. He stayed loyal. One thing you learn playing basketball is that to truly become great at this game, you have to learn to adapt to other people’s personalities and temperaments, their weaknesses and strengths. If I know someone is prone to chucking the ball as soon as it touches their hands, I’m going to spend most of the game hawking for rebounds or trying to pass them the ball when they’re in a good position to score. I’m not going to force my way onto the other team or freeze the person out like they’re MJ in the 1985 All Star Game. Trust and loyalty are foundational to basketball. Which is what makes this so hard to stomach. It’s hard to think of an athlete who forged more of a symbiotic relationship with the city of Toronto, especially when so many players have treated the place like Siberia. On “LOYALTY.”, Kendrick raps, “Is it unconditional when the ‘Rari don’t start?” That line represents loyalty through thick and thin. In the case of the Raptors and DeMar, only one side stayed true to that axiom. It’ll be hard for me to look at the Ujiri administration in the same way after this summer.


Pasha Malla, Author

‘Smooth Operator’ – Sade

Since their early days of $5 seats at the Skydome, the Toronto Raptors have hosted a lot of smooth players — Doug Christie, Tracy McGrady, even Keon Clark at his swooping, noodly best. But none was ever as smooth as DeMar DeRozan, and few players in league history, save maybe George Gervin himself, have been as fluidly ruthless with the basketball. DeMar doesn’t drive to the hoop, he glides like a hawk on a breeze. His jumper’s buttered silk. He moves in space with minimum waste and maximum joy—yeah, Sade. That’s right. That’s him.


Sarah MacDonald, Writer

‘Now & Forever’ – Drake

There will be—I assume—quite a lot of Drake songs on this list. DeMar DeRozan’s ascent as a Toronto Raptor during this decade happened to coincide with The Boy’s, which is maybe both a blessing and a curse, because we’ll always see them both woven tightly together into the fabric of Toronto’s basketball culture. But DeMar’s gone. 

Getting attached to a major sports player is tough. You don’t know them, really, and they certainly don’t know you but you’re bound to each other through the love of this one game and the pulsing, intoxicating glimpse of joy that comes with it. 

“Now & Forever” is moody like DeMar; gives no fucks like DeMar; escapes to grind, sweat, and persevere like DeMar. Yet, for all the bravado Drake exerts on the track, it’s also tender and generous, wanting to bring it back home, whatever it is, but you have to let him do what he wants to do. DeMar was like that. He had us. He wanted to have us. We trusted him to do what he needed to do and he did it with care, with generosity, beyond being a multi-million dollar paid basketball player. He gave a shit. But he’s not going to get a chance to bring it home to us now though; a championship win, pride, recognition of our city as real, honest-to-god contenders. 

DeMar’s not looking back, that’s not his style. People like DeMar—what he means and does for an entire country—aren’t simply blips, temporary impressions. He’s forever. 


Sean Menard, Director (The Carter Effect)

‘Graduation (Friends Forever)’ – Vitamin C

The song I choose is my Karaoke go to. The artist who wrote this song took the academia nostalgia market by storm, she couldn’t possibly have known that just 18 years later it would play perfectly for how Toronto should feel towards DeMar. The city is ready to move on (to the NBA Finals) but as we go on, we will remember, all the times we, had together. Toronto and DeRozan will still be: #FriendsForever


Alex Wong, Writer

‘You Came Up’ – Big Pun ft. Noreaga

It almost became a running joke by last season that every single writer in Toronto had written at least three “DeMar DeRozan works really hard and improves his game every season” features. It almost reads like a tired trope: athlete works really hard, becomes really good. But this wasn’t just a narrative with DeMar, it was the actual reason why he went from a lost rookie to a multiple time All-Star and All-NBA player. That’s the thing I’ll remember most about DeMar: he worked his ass off, and came up. 


Paul Murphy, DJ (Skratch Bastid)

‘No Vaseline’ – Ice Cube

I picked this because the (non-stat related) thing I’m going to miss most about DeMar is his extra-Compton scowl after he did something nasty on the court. This song is like the musical manifestation of that scowl, or perhaps it’s forefather! Ice Cube wrote this after he split with N.W.A., and I wouldn’t be surprised if DeMar channeled this energy in his first game against his former team. 


Cabral Richards, Host (Cabbie Presents)

‘Down As A Great’ – Nipsey Hussle ft. Kirko Bangs

“Legendary moves, leader of my crew/heavy is the head that wear the crown, that sh*t true/Do it like Nip Hussle, that’s to fill some big shoes/and what good is excuses when the f*ckin’ rent’s due?” Quiet confidence, diligently working on his craft, not nearly as flashy as his peers, but holds the respect of the entire game. There’s a lot of Nipsey Hussle’s vibe in DeMar DeRozan. Using the platform of hip hop, Nipsey delivers tales illuminating the struggle from the streets of Los Angeles, while translating into commerce, while feeding the culture. DeRozan uses his platform as a basketball player to raise awareness for Lupus, raised the profile of Toronto (signing a max deal to stay for five years in 2016) and more recently millions of people struggling with their own minds. ‘Down As A Great’ by Nipsey Hussle captures the essence of DeMar DeRozan; laid back, determined and self made.


Emma Healy, Poet

‘Any Day Now (My Wild Beautiful Bird)’ – Chuck Jackson

Just a few quick questions: Is it ever possible to feel love without the promise of its eventual loss looming on the periphery? Is it revolutionary or foolish to try and do something you really care about inside a capitalist framework that ultimately counts all unprofitable emotions as frivolous, and all the people who feel them as infinitely replaceable? Do you need to hold onto your pain to make great art, or is it destined to eat your work from the inside if you can’t let it go? Are sports supposed to be a distraction from your feelings or a container for them? 

My favourite DeMar DeRozan moments are the ones where he seems to untether himself from all context – floating down the court, or hanging in the air for an impossible extra half-second after shooting a 3. These feel like analogues for the brief moments of actual joy I’m sometimes able to from my own clinically anxious mind if I work really hard: the times when I’m able to stop replaying my past or interrogating my future long enough to meet myself in the present. Sometimes, in moments of acute game-time crisis with the Raptors, I thought I could see Derozan struggling with this same challenge, and I felt for him; I wanted him to succeed, and I still do, and I sometimes worry that there is something about Toronto that makes it extra hard to do that here. But of course, I’m projecting. Basketball is a business, a team is not a city, and Demar Derozan is a human being, not a symbol. That’s what made him such a good symbol. I hope he is allowed to grow into his complexity in San Antonio. He deserves it.


Sasha Kalra, VICE Canada

‘Started from the Bottom’ – Drake

No song encapsulates the DeMar DeRozan era quite like ‘Started from the Bottom’. He was drafted ninth overall in 2009—well after some notable busts—and played one season with Chris Bosh before the latter departed for South Beach. It was then that he infamously tweeted “Don’t worry, I got us…” and proceeded to develop into a star.

Did anyone see DeRozan developing into the player he is today? He spent time jacking up inefficient shots on some terrible Raptors teams during his formative years, and that could’ve easily derailed him. But the guy just kept working, and kept adding new facets to his game until he became a good player, and then an All-Star, and eventually an All-NBA player. When Bosh left, that was rock bottom, and DeRozan helped bring the team to heights they’d never experienced before. Build the guy a statue ASAP.


Brian Kim, DJ (Your Boy Brian)

‘100′ – The Game ft. Drake

The first track that pops into my head when I think of DeMar is ‘100’ by The Game and Drake. A track featuring a union of artists that hail from Compton and Toronto respectively couldn’t be any more symbolic of DeMar’s tenure with the Raptors. Game’s first verse talks about someone asking him to put a hit on a visiting Drake and his OVO crew… instead he grants them protection. “I got a vest for 40, a vest for Hush / A vest for every n——- with an owl on his chest and what”—Compton looking out for the 6ix just like Deebo did when he tweeted “Don’t worry, I got us…”

Hearing those bars, and reading that tweet, filled me with pride. Because I grew up a middle class fan of Hip-Hop, the city of Compton is a place that had an almost mythic quality to it. It was dangerous, it was cool, It was an urban Narnia. To have two of its native sons, one a rapper, and one a basketball player, put on for Toronto so hard felt validating. And part of what made it so depressing when we traded our guy.

DeMar felt betrayed, I think we all felt a bit betrayed by the news. On the chorus of ‘100’ Drizzy raps “All I ever ask is keep it 8 more than 92 with me, 100” – which takes on a newfound poignancy in hindsight of last week’s deal. I guess I’ll eventually get over it but I’ll also probably always remember the past five years as my happiest as a basketball fan. And regardless of whether the team kept it 100 with him, DeMar always kept it 100 with us.


Ennis Esmer, Actor

‘Nubeginning4’ – Quelle Chris ft. Machine

When I first heard about the trade I was trying to understand it and rationalize it because on paper we won that deal hands down. On paper Kawhi reports and isn’t hurt and plays like the top 5 player he is and we have our best season ever. But a few days later all I just got really sad about DeMar leaving. We’re so insecure and worried here as fans, but DeMar chose Toronto. And it’s not a long NBA history in this city. Everybody great has left. Damon. Vince. TMac. Bosh. But he made it clear we were his first choice. And he put us on the map. Him and Kyle. When Vince was famous it was because of Vince. We won one playoff series with Vince. But the team actually played its best basketball ever with DeMar and Kyle. Five straight years in the playoffs. Conference finals. Two wins from the championship. Consistently breaking win records. Finishing 1st in the conference. And my heart breaks for the fact he chose Toronto, and we traded him. He chose Toronto and became the best Raptor ever, worked every season to upgrade his game, and in a painful irony, that made him easier to trade. That hurts. But it’s time to turn the page. For him. And for us. And as the song says, there’s a new beginning for everything.


William Lou, Writer

‘November’ – Tyler the Creator

His intentions were always genuine, there was never a time that I quite felt assured with DeRozan leading the Raptors, especially during the playoffs. I love this man dearly for how much he loved the city and the franchise, but sports are stupidly binary – you’re either good enough or you’re not, and I always doubted if a flawed star like DeRozan really did “got us” (What if ‘Who that Boy’ is rhetorical?’).  

The last five years were characterized by the same cycle: intrigue over DeRozan’s yearly offseason improvement, exuberance over regular season success, and disappointment when it counted most. After last year, when DeRozan was a total no-show against Cleveland after we swore he was an MVP candidate, we just couldn’t pretend any more. That makes me sadder than anything else, because it was a good thing, but we just got exhausted. 

‘November’ is a sad song about happy memories. It’s about the small breaks from anxiety and self-doubt where we’re happy and content and not worried about real shit like beating LeBron. It’s about throwaway regular season games in November, when DeRozan could scale the Stifle Tower, when the Raptors win care-free basketball games, and it’s all good. (“Hawaiian shirts in the Winter, cold water, cold water, Yeah, take me back to November, wassup. Can we go back to November?”)


Jake Goldsbie, Actor

‘Sick, Later’ – Bomb The Music Industry

Not just because the title is how I feel about the trade now. I’m kind of lyric picking I guess but the idea of hoping to see DeMar again under the glow of lights seems appropriate. As does the very Raptors fan describing “I’m such a guarded guy cause I’ve been hurt too many times.” We ARE guarded guys. We’ve been hurt too many times!


Doug Smith, Reporter, Toronto Star

‘Good Riddance (Time of Your Life)’ – Green Day

I’m not sure there’s a song more fitting. I covered Gretzky’s last game in New York, they played it then and it stuck with me. 


Steve Sladkowski, Musician (PUP)

‘Headlines’ – Drake

For me, the We The North era Raptors will forever be tied to the rise of Drake and Toronto’s reemergence on the global stage of music & pop culture. From the (admittedly-exhausting) “with my woes!” after seemingly every DeMar midrange J, I can’t think of anyone other than Drake whose music best represents one of the two best Raptors to lace up a pair of sneakers. 2015 was the Raptors and Take Care… it just was, y’know? The song has to be “Headlines” — “those my brothers/I ain’t even got to say it/it’s just something they know/they know/that the realest on the rise.” That’s DeMar. He had us. It’s shocking to realize he won’t be wearing Raptor red next season… 


Blake Murphy, Writer

There’s No ‘I’ in Team’ – Taking Back Sunday

Admittedly, this is a little dramatic. Originally a response to Brand New’s “Seventy Times 7,” “There’s No ‘I’ In Team” is the quintessential end-of-friendship song. There are some biting lyrics that really hit home here, especially if you think of certain parts of the song (the chorus, namely, as well as the first two call-and-response verses) as a post-trade conversation between Masai Ujiri and DeMar DeRozan. No, trading a star player is not quite the same as trying to steal a bandmate’s girlfriend, but it’s clear that DeRozan felt like this Raptors core would be given the chance to go down together and that Ujiri felt he had to pull the trigger, leaving himself to hope that in time DeRozan will forget the unforgivable. This, then, is not so much an ode to DeRozan–I felt a little weird calling on the litany of wistful, hiraeth-inducing love songs that make up the bulk of my playlists–but an “it’s alright, I understand.” Plus, screaming the backing vocals while driving around aimlessly is tremendous therapy, if you need it.


Katie Heindl, Writer

‘Seasons (Waiting On You)’ – Future Islands

This song has always had it all for me. It’s triumphant, sad, a little bit angry, pleading and purgative—the beginning to something, or an end. The main thrust is waiting on someone to change and what it means to be the one waiting. There’s a lot of development and depth, which to me sums up DeRozan, and the feelings around him leaving.

Every year he came back improved, ready, willing, clearing away any holdover doubts from the season before. Ready to go through it all again for the promise of something even better. From a fan’s perspective, there was the waiting to see how the changes might pan out in the long run. And in the most literal sense, between seasons in basketball changes get made and players get traded (“You know when people change/they gain a piece but they lose one too”).

There was so much give and take with DeMar and I think in the last few years of his career it was him giving everything here, maybe too much. There’s an effort and struggle with this song and ultimately the realization that some cycles don’t serve us and change is inevitable, even if it hurts. DeMar not being in Toronto when this season starts is going to feel strange and sad, and there are still questions of what he could and would have done with another year in the city but he’s moved on, and maybe this next revolution in his career lifts him up even higher.


To DeMar, From Toronto: A Goodbye Playlist for DeRozan