Drake and DeMar DeRozan: A Timeline of Their Relationship

Drake and DeMar DeRozan were once great friends, but it seems like Drake's feud with Kendrick Lamar now has them at odds.

Over the weekend, Drake sat courtside for a game between the Toronto Raptors and the Sacramento Kings. During the game, Drake gave the six-time NBA All-Star nasty looks, allegedly called him "pussy," and dissed him when he spoke to Raptors commentators.

DeRozan responded during the postgame conference and he also seemed to respond on Instagram, posting a movie clip suggesting Drake was just acting tough.

Everything was all good between these two before DeRozan made a cameo in Kendrick Lamar's "Not Like Us" music video and danced on stage alongside K. Dot at "The Pop Out" concert. While DeRozan did play for Toronto, he was born and raised in Compton and clearly seemed to be picking sides.

In light of their latest back and forth, we took a look at the history between Drake and DeMar DeRozan...

2009: DeMar DeRozan Gets Drafted to the Toronto Raptors, Drake Drops So Far Gone

The city of Toronto had a huge year in 2009. The Toronto Raptors selected the six-foot-six-inch forward from USC as the ninth overall pick in the NBA Draft. Meanwhile, Drake dropped his breakout mixtape, So Far Gone.

Demar DeRozan spent nine seasons with the Raptors, becoming the franchise's all-time leading scorer. He also led the Raptors to five playoff runs, including an Eastern Conference Finals appearance in 2016.

Drake, on the other hand, put Toronto on the hip-hop map, bringing eyes to the 6 through his music on his way to becoming his generation's biggest rapper.

2013: Drake Becomes Toronto Raptors' Global Ambassador

The Toronto Raptors announced Drake as their new "Global Ambassador" in 2013, which was reportedly an unpaid position that had him help grow the team's brand. Over the years, Drake boosted the team's visibility by doing things such as enhancing the Raptors' home arena with a nightclub, helping design the team's jerseys, and more. Drake working closely with the team and his connection to DeRozan only strengthened their friendship.

2016: Drake and Demar DeRozan Land on the Cover of SLAM Magazine as the "6 Gods"

SLAM Magazine featured Drake, Demar, and fellow former Raptor Kyle Lowry on its April 2016 cover titled "6 GODS." In the article, DeRozan and Lowry claimed the rapper was "our man" and that he's "really supportive" of everything they were doing. DeRozan also revealed he lived close to Drake in Los Angeles, and they hung out with each other almost every summer.

2018: Drake Shares Appreciation Post After DeMar DeRozan Gets Traded to the San Antonio Spurs

Despite DeRozan being one of their best players since the days of Raptors legend Vince Carter, the Canadian franchise traded him to the San Antonio Spurs in exchange for Kawhi Leonard and Danny Green in 2018. The move rocked the NBA world, and Drake shared an appreciation post on his Instagram for DeRozan and his contributions to the team and city.

"To my brother @demar_derozan I want to say 10 million thank you's on behalf of YOUR city," Drizzy wrote in his post. The move would turn out great for the Raptors as Leonard led the team to their first championship in 2018.

2021: Drake Supports DeMar DeRozan After Spurs Trade

During a recent interview on Club Shay Shay, DeRozan revealed the role Drake in his life in the aftermath of being traded by the Raptors. According to DeRozan, he spoke to a supportive Drake for hours.

"Man, we just really sat there, and besides basketball and everything, just the reassurance of like that was my partner, that was a friend of mine that was like 'Get away from everything. I know it's crazy,'" said DeMar. "I couldn't even turn on the TV that day. Phone was going crazy. I just went over there, and we sat and talked for hours. And more than anything just him being there for me as a friend first and foremost."

He continued, "No matter what, when it come to him, he'll forever have a friend in me and loyalty out of me because he cared. He was there for me when everything was kind of going crazy."

May 2024: DeMar DeRozan Gets Mentioned in Kendrick Lamar's "Not Like Us"

Kendrick Lamar delivered a lethal blow to Drake in the scathing diss track "Not Like Us." In one of his verses, Lamar name-dropped DeRozan and expressed his happiness that he was traded because he believed the Raptors and the city of Toronto didn't "deserve" him.

"I'm glad DeRoz' came home, y'all didn't deserve him neither," rapped Lamar. DeRozan and Lamar both hail from Compton, California.

June 2024: Demar DeRozan Dances on Stage Alongside Kendrick Lamar at "The Pop Out" Concert

If the name-drop wasn't enough, DeRozan added more fuel to the fire by getting on stage while Kendrick Lamar performed "Not Like Us" at "The Pop Out" concert in Inglewood, California. DeRozan was not the only baller in attendance. LeBron James, another one of Drake's close friends, also attended the concert (though he did not hop on stage). After the concert, Drake unfollowed LeBron and DeRozan on Instagram.

July 2024: DeMar DeRozan Makes Cameo in "Not Like Us" Music Video, Later Says Kendrick Is "Basically Family" and Drake is "Still My Man"

DeRozan took things to another level when he appeared in the official music video for "Not Like Us," where he crouched down and looked deeply into the camera, seemingly picking Kendrick's side in the vicious feud. In an interview with Fox40, DeRozan explained his cameo while stating that people still love Drake, including himself.

"We love Drake, we always can play him," said DeRozan. "Kendrick been a friend of mine, family. Damn near family, for a long time, for a while. We're from the same city, we grew up damn near in the same neighborhood...It's always been there. It hasn't always been publicized, but, you know, that's basically family."

In another interview, this time with The Sacramento Bee, DeRozan said he's still friends with Drake and that the rap beef is all in music and entertainment at the end of the day.

"Drake's still my man, still my man, none of it changed," DeRozan told the newspaper. "It's so easy to get overlooked and look at it for what it looks like, but at the end of the day it's music, entertainment. Two of the biggest rappers in the world went at it from a competitive standpoint, and they battled it out."

October 2024: Drake Calls Out Former Friends Who Were Disloyal and Switched Up On Him

Drake had some words for his allies who seemed to support Kendrick Lamar amid their beef. Although Drake didn't mention anyone by name, fans assumed his list included people like Rick Ross and DeMar DeRozan.

"My real friends are definitely in the building," he said. "But let me tell you that you're going to come to a point in life where people you thought were friends, or people you thought were close to you switch up."

He continued, "They might stab you in the back...They might do a lot of things to you...You'll come to that realization wherever you're at in life, you'll probably be there or been there — that's how life is. Sometimes it's you and you alone, by yourself. Sometimes, it's you alone with your thoughts."

November 2024: Drake Disses DeMar DeRozan During Raptors Broadcast, DeMar Responds During Postgame Interview

Last Saturday, the Raptors retired Vince Carter's jersey during a game against DeMar DeRozan and the Sacramento Kings. The game was DeRozan's first time back in Toronto since his appearance in "Not Like Us," and Drake was sitting courtside next to OVO Chubbs.

During the game, cameras caught Drake grilling DeRozan while he was on the court. He seemingly looked away when DeRozan glanced in his direction, and later, he called DeRozan a "goof."

Drake went even further and dissed the former Raptor while speaking to Raptors commentators midgame saying, "If you ever put up a DeRozan banner, I’ll go up there and pull it down myself."

Things got more feisty when DeRozan missed a game-winning shot, and cameras caught Drizzy calling him a "pussy."

DeRozan was asked about Drake's jersey comments in the post game conference and he responded saying the rapper has "a long way to climb to take it down." He also posted a clip from the movie Friday about the character Deebo on his Instagram, insinuating that Drake only acts tough when other people aren't around. Deebo is also DeRozan's nickname.