Drake is one of the most powerful men (monetarily speaking) on Earth. So what does "the best he's ever had" look like? Take a look:

2013

Cyn Santana // Model

Drake met the Instagram star on the set of 2 Chainz's No Lie music video.


2014

Rihanna // Singer

Drake and Rihanna first got caught kissing in 2009. Their long on-and-off relationship ended completely in 2014.

Zoë Kravitz // Singer, Actress & Model

After many relationship rumors, Zoë confirmed that Drake is strictly a friend to Complex magazine in April. I’m very flirtatious. [But] he’s family to me. He’s a really, really awesome dude.”

Photo cred - Instagram

Shaye G // Instagram Model

Last fall, Drake's rumored side girl (he was dating Rihanna) claimed that he was stalking and threatening her via text messaging.

Photo cred - @lira_galore

Lira Galore (Mercer) // Model & Actress

Last year, tabloids reported that Drake lured former stripper Lira Galore away from Houston Rockets player Pat Beverley. She was then engaged to Rick Ross, but broke it off recently.

Lesha Mariee // Model

According to some gossip websites, this Instababe is a well-known groupie in the industry. Before Drake, she supposedly hooked-up with Chris Brown, Trey Songz, Future and many athletes. She is now expecting her first child.


2015

Bernice Burgos // Business woman & Model

Drake was photographed kissing this woman last march while vacationing in Australia.

Serena Williams // Athlete

Drake and Serena Williams have been photographed together this past August, 4 years after their break up.

Ravie Loso // Instagram model

Drake was spotted with her many times this fall. She was his date at Kendall Jenner's 20th birthday bash in Hollywood.

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