Graham was born in Toronto, Ontario, the son of Dennis Graham, a drummer who worked with Jerry Lee Lewis; he is the nephew of musicians Larry Graham and Teenie Hodges. Graham's father is African American (a native of Memphis, Tennessee) and his mother, an educator, is a white Jewish Canadian. His parents divorced when he was five, and he was raised by his mother in Toronto's wealthy Forest Hill neighbourhood, attending elementary school at Forest Hill Public School, and high school at Forest Hill Collegiate Institute, where he began acting, but did not graduate. He also spent many summers with his father in Memphis, Tennessee.
In 2001, Graham began his acting career, playing the role of Jimmy Brooks, a character on Degrassi: The Next Generation. In the show, Brooks is a basketball star who became physically disabled after he was shot by a classmate. His role on the show ended in 2009, when producers cut the entire Degrassi staff for a new group of actors.
In February 2006, Drake released his first mixtape Room for Improvement. It was made available via his website and official MySpace page. From the success of his first mixtape, he later began releasing more, capitalizing from the buzz.
In 2007, he released Comeback Season to much critical acclaim and praise. It was from here on where Drake started gaining popularity when he did his first song with Lil Wayne, a remix of the already popular song "Man of the Year" which Wayne didn't rap in but had ad-libs in the end of the song. Also in 2007, Drake became the first unsigned Canadian rapper to have his music video featured on BET when his first single, "Replacement Girl" was featured as the "New Joint of the Day" on April 30, 2007. In 2008, he released Heartbreak Drake, another popular mixtape release which helped gain more acclaim and buzz for Drake. After the minor success of Heartbreak Drake, Drake collaborated on a mixtape titled, Thomashow Time, which featured his friend and fellow rapper Thomashow. So Far Gone, which included Drake's mentor Lil Wayne, and members of Young Money, was released in 2009.
While working on his mixtapes and his album, Drake worked with Lil Wayne, Jay-Z, Kanye West, Trey Songz, Robin Thicke, Little Brother, Mary J. Blige, and Jamie Foxx. Drake has also written for Jazz Cartier, Bishop Brigante, and Dr. Dre.
He achieved success before signing to a major record label, according to his management Hip Hop Since 1978. In June 2009, it was revealed that an unauthorized album entitled The Girls Love Drake and credited to Drake was up for sale on iTunes. A lawsuit is planned against the label.
On the Billboard Hot 100 chart of July 4, 2009, both "Best I Ever Had" and "Every Girl" by Young Money Entertainment entered the top ten at positions 3 and 10 respectively. Drake is only the second artist to have his first two top ten hits in the same week. The first was fellow Canadian Nelly Furtado who entered the top ten in 2001 with "I'm Like A Bird" the same week as Missy Elliott's "Get Ur Freak On", a remix of which included a credited contribution from Furtado.
On June 29, 2009 it was confirmed Drake signed a record deal with Young Money Entertainment. This followed what Billboard purported to be "one of the biggest bidding wars ever". He plans to release his official debut album, Thank Me Later, in late 2009, and has confirmed collaborations with the likes of Kanye West, Jay-Z, Danny! and Lil Wayne. Drake is currently touring with Wayne and other rap artists on the America's Most Wanted Tour.
In 2008, Drake spoke about his past relationships on a song called "Deceiving" using each verse to address different women. In Verse 1, he spoke about video-girl Dia Edwards. In Verse 3, he spoke about classmate Alisha Phillips.
He then spoke about his past relationship with Keshia Chanté on the Verse 2 of his song "Deceiving", referencing Chanté's mother, Tessa, stating "when I say I'm serious, you claim your only teasing" and "What up Tessa? I love you like my own mama, and your daughters getting grown mama, and me, I'm just here working, waiting, patient for her to be ready for love and leave alone drama"
In May 2009, Drake finally spoke with MuchMusic about his song "Deceiving" and addressed speculation of his past relationship with Chanté, "Would I call Keshia Chante an ex? I'd be proud to say she is an ex. I'm proud to say we had our time, when we were, like 16 years old. She's great. She's one of the first people in the industry that I met, we just connected."
In June 2009, Drake did two remixes to Chante's song "Fallen" where he addresses his love for her, on Version 1 he raps "Keshia, Keshia, do you remember the old us? They said we'd never be together that's what they told us. Immature kids, to entrepreneur kids." then on Version 2, he raps "you just hold it down for your boy until the plaques arrive, that's why I love you."
MuchMusic later asked Chanté on how she felt about what Drake. She kept mum, later saying, "I will love that man unconditionally for the rest of my life. He knows what it is. We have history. I've known him since I was a little girl. We just have a love/hate relationship, so I prefer to love him from afar."
Online rumors swirled stating that Drake was in a relationship with Rihanna. Both parties denied that claim, with Drake stating "we're just good friends.".