Pick a Day

Aubrey Drake Graham is born in Toronto. After a stint on the TV show Degrassi: The Next Generation, he becomes a superstar rapper under the name Drake.

Drake makes his professional debut with a 30-minute set at the Kool Haus in Toronto opening for Ice Cube. It earns him $100.

Drake and Chris Brown are involved in a fight at a New York City nightclub, with Brown accusing Drake of throwing a bottle at him. They had beef over Rihanna, whom they both dated.

Drake places an astounding 14 songs in the Hot 100, thanks to the release of his mixtape If You're Reading This It's Too Late. The Beatles are the only other act to accomplish this, with 14 songs on the tally for a week in April 1964. Drake goes on to place 27 songs on the chart dated July 14, 2018, and 42 on May 24, 2026.

Drake releases "Hotline Bling," the first single from his album Views. He doesn't rap in the song, but it still wins Grammy Awards in two rap categories, which Drake doesn't show up to accept because he feels it's really a pop song.

When Drake doesn't promote Meek Mill's album on Twitter, Mill accuses him of using a ghostwriter, tweeting: "Stop comparing drake to me too.... He don't write his own raps! That's why he ain't tweet my album because we found out!" A feud ensues when Drake releases the diss track "Charged Up," which Mill says is "Baby lotion soft."

Following the release of his album Views, Drake places a record 20 songs on the Hot 100, besting Justin Bieber's mark of 17 on December 5, 2015.

The National Transportation Safety Board (NTSB) warns against the trend of jumping out of moving cars and dancing to Drake's "In My Feelings."More

Drake breaks his own record for most entries on the Hot 100 at once when he places 27 songs on the tally following the release of his album Scorpion.

Drake wins Artist of the Decade at the Billboard Music Awards.

Kanye West and Drake end their long-running feud when they perform together at the Free Larry Hoover concert.

Drake, a longtime critic of the Grammy Awards, turns down his two nominations, joining The Weeknd in boycotting the awards. Drake feels he's being pigeonholed into hip-hop categories when he's really a pop artist; The Weeknd has beef because he wasn't nominated the previous year for his album After Hours or song "Blinding Lights."

The first truly believable AI-generated song appears online, posted to TikTok by an anonymous user. It's called "Heart On My Sleeve," and mimics the voices of Drake and The Weeknd. It quickly spreads to streaming services and is continually taken down and reposted, raising the issue of copyright with AI music.

Kendrick Lamar disses Drake in the song "Like That," igniting a high-profile feud that gets ugly. Lamar wins the popular vote in this rap battle when his diss track "Not Like Us" goes to #1.More

Kendrick Lamar's "Not Like Us," a scathing diss track directed at Drake, goes to #1 as their feud comes to a head.

Diss tracks are protected speech, a judge rules in Drake's defamation lawsuit against Universal Music Group, which released and promoted Kendrick Lamar's "Not Like Us," a song where he says very hurtful things about Drake. "The average listener is not under the impression that a diss track is the product of a thoughtful or disinterested investigation, conveying to the public fact-checked verifiable content," the judge explains.

Drake's albums Iceman, Habibti and Maid of Honour debut at #1, #2 and #3 in the US, making him the first artist to occupy the top three spots. Over on the Hot 100, 42 of the 43 songs make the chart, a new record. Another milestone: Iceman gives Drake 15 #1 albums, surpassing Jay-Z for the most among male solo artists.

Dusting himself off from his feud with Kendrick Lamar, Drake celebrates the release of his long-awaited album Iceman with a fireworks display at midnight at the CN Tower in Toronto, which is iced-out for the occasion with 75 projectors. He also surprise drops two more albums: Habibti and Maid of Honour; a total of 43 tracks.