Drake and Kanye Song Collaborations: A Complete Timeline Before Their Feud

To say that hip-hop has had its share of feuds would be an understatement. From 2Pac vs. The Notorious B.I.G. in the early '90s and 50 Cent vs. Ja Rule at the turn of the millennium to the more recent Drake vs. Kendrick Lamar beef, fans have always had something to talk about and sides to pick. 

Drake and Kanye West's feud is complex, involving a series of disagreements that evolved into a rivalry. However, unlike clashes between other hip-hop artists, their musical relationship is characterized by subtle digs at each other in lyrics and interviews rather than brutal, in-your-face musical disses and lyrical insults. While the conflict has ebbed and flowed for over a decade, it has never gotten ugly and appears more like a professional rivalry than a personal issue, with both artists clearly admiring each other's work and talent. Let's explore their relationship in more detail, from their first interactions to the present day.

The first professional interaction between the two hip-hop titans was in 2007, when Drake rapped over the instrumental of West's song "Barry Bonds" from his Graduation album. Drake included "Barry Bonds Freestyle" on his Comeback Season mixtape, which was self-released on Sept. 1, 2007. It's unclear how he obtained the track before West officially released his album around six weeks later. 

This was Drake's way of showing he can play with the big boys, and he did it again the following year. "Swagger Like Us" was an all-star collaboration featuring Ye (formerly Kanye West), T.I., Jay-Z, and Lil Wayne, and Drake freestyled over it to show his established peers that he was coming up in the music scene. Another subtle jab from Drake followed in 2009, when he released a remix of West's "Say You Will," called "Say What's Real." 

Their first in-person encounter also occurred around that time, with Drake describing West a few months later in an MTV News interview as "the most influential person, as far as a musician, that I've ever had in my life."

Drake and Kanye's collaboration history spans over a decade. As a broader audience began to recognize Drake's talent and potential, so did West. In fact, he directed Drake's first-ever music video, 2009's "Best I Ever Had." A few months later, they had their first musical collaboration, alongside Eminem and Lil Wayne, on the song "Forever," featured on the soundtrack of Lebron James' documentary More Than a Game. A string of Drake and Kanye song collaborations followed, showcasing the chemistry between the two rappers and cementing Drake's status as an established artist who can hold his own among his established peers.

After this initial honeymoon period, things started to turn sour between the two. Drake was seen at a club with Ye's ex, Amber Rose, sparking rumors. During a 2011 interview with Tim Westwood, Drake also implied that West and Jay-Z got the idea for their collaboration, Watch the Throne, from his planned joint album with Lil Wayne.  "I heard some other guys are coming out with an album, too," he said at the time. "There's two other rappers that are coming out with an album together. I don't know where they got that idea."

Things escalated quickly following these events. Later that year, in an interview with The Source magazine, Drake unequivocally stated: "My goal is to surpass everything he's accomplished. I don't want to be as good as Kanye — I want to be better. Then, in 2013, Ye admitted that Drake's planned collaboration with Lil Wayne was indeed the spark that led to his wildly successful joint album with Jay-Z. "Me and Hov would've never made Watch the Throne if [Drake] wasn't putting pressure on us like that," he told MTV at that time.

After these competitive jabs, the atmosphere between the two again turned friendly. As Drake put it, in an MTV News interview: "I think me and Kanye have wanted to express our respect for each other for a long time, and sometimes rap, the business, the competitiveness, and just the heart behind it forces you to not talk to the people you quietly admire." 

They also had their first collaboration in many years, on Big Sean's song "Blessings." Around that time, during a Breakfast Club interview, West also teased the possibility of a joint album.

West produced five albums during the 2018 Wyoming sessions, including his own Ye album. During an appearance on Lebron James' The Shop talk show, Drake mentioned that he was invited to Wyoming by West for a potential collaboration, but the situation evolved into a dispute over the beat from the song "Lift Yourself." While they discussed Drake buying it for $3 million, West ultimately used the beat himself.

The complicated relationship between the two hip-hop giants goes on to this day. A temporary reconciliation for the Free Larry Hoover Benefit Concert at the Los Angeles Memorial Coliseum on Dec. 9, 2021, was followed by subtle digs between the two on social media. This seems to fit the pattern for their relationship, which includes periods where they show mutual respect and even collaborate professionally, followed by subtle disses.

Their rivalry was also fueled by the fact that they both released albums within the same year (2021). While both albums went straight to the top of the Billboard Top 200, Drake's garnered significantly more sales and streams.

The personal and professional rivalry between Drake and West still probably has a few episodes in store. Given what has happened over the past 18 years, it's safe to expect periods of musical collaborations and nice words, followed by less direct attacks between the two in interviews and on social media. However, as in any other field, having a rival that's there to profit from your mistakes can be a huge motivator, and the winners of this battle of hip-hop titans are ultimately the fans.