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Dennis' limited finances and legal issues caused him to remain in the United States until Drake's early adulthood.

Prior to his arrest, however, Dennis would travel to Toronto and bring Drake to Memphis every summer.

In 2007, he released his second mixtape, Comeback Season.

Released from his recently founded October's Very Own label, it spawned the single "Replacement Girl", featuring Trey Songz.

were critically and commercially successful; the former earned him his first Grammy Award for Best Rap Album.

When asked about the mixtape, Drake described the project as "pretty straightforward, radio friendly, [and] not much content to it." The mixtape was released for sale only, and confirmed to have sold over 6,000 copies.This caused Jas Prince to gift Lil Wayne the song, which prompted the rapper to invite Drake to Houston in order to join his Tha Carter III tour.Despite the collaborations between the duo, Drake was yet to be signed by Young Money Entertainment.Drake's parents divorced when he was five years old.After the divorce, he and his mother remained in Toronto, while his father returned to Memphis, where he was incarcerated for a number of years on drug-related charges.

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and contains the Grammy Award winning number-one single "God's Plan", and the bounce-infused number one singles "Nice for What" and "In My Feelings".

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