Drake's Five Saddest Miami Moments

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3. When Diddy punched him in the noggin outside LIV.

Drake loves the VIP section just as much as the next guy. But in 2014, his night out at Miami Beach mainstay LIV turned south when news broke that Drake was sent to the hospital following an altercation with P. Diddy. It happened at a time in Drake's career when it seemed as though he might have finally earned something approaching street cred (we were just beginning to forget about the Degrassi years). The altercation was allegedly caused because Puff Daddy felt he had been bamboozled out of the "0 to 100/The Catch Up" instrumental, but it could also have easily been because Drake wouldn't stop stealing Diddy's phone and Tweeting out: "#boobs," since that seems like something he'd find hilarious. 

2. When the American Airlines Arena wouldn't let Drake into the Heat locker room.

In 2013, when the Miami Heat clinched the NBA championship over the San Antonio Spurs, Drake was there to witness it all, cheering along with all the enthusiasm of a caffeinated soccer mom. After the game ended, he went back to the locker room to help the Heat celebrate and drink some of that champagne LeBron and company were popping. But, tragically, when he reached the door, he was not allowed in. The rapper was informed by an elderly security guard that the entrance was only for media, to which Drake replied, "I am media," which is basically the hip-hop equivalent of Jeb Bush's infamous, "Please clap" line. Not shockingly, that didn't work, and Drake had to listen to all the fun from outside while (presumably) scrolling through his ex-girlfriend's Instagram feed. The whole thing was filmed and went viral almost immediately. Asked about the security guard who gave him the cold shoulder, Drake later told ESPN, "I don't blame him. He was like 89 years old. I understand, hats off to that gentleman who was doing due diligence as security," Drake said, before (presumably) diving back into his ex's Instagram feed. 
1. When, after he finally did catch up with LeBron, he accidentally turned himself in a meme.

Remarkably, the night of the 2013 NBA Championship only got sadder for Drake after he was initially refused entry into the locker room. Because, when he did finally catch up with LeBron James and the rest of the Miami Heat celebrating their shiny new rings at the SoBe club, Story, he ended up taking a photo that would haunt him for years to come. It's one of the most recognizable Drake meme's out there — and also the most damaging to his street cred. In the pic, LeBron throws an arm around Drake, who's smiling like he's being tickled by 1,000 invisible ghosts. Drake's left hand is raised in an, Oh, stop it, you silly goose! sort of way. It also doesn't help that he's — for some reason — wearing your dad's favorite Polo. It's vintage Drake, proving once again that money isn't a vaccine against awkwardness. 

Drake. 6:30 p.m. Tuesday and Wednesday, August 30 and 31, at the American Airlines Arena, 601 Biscayne Blvd., Miami; 786-777-1000; Tickets cost $95 to $1,715 plus fees via

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Ryan Pfeffer is a contributor and former Miami New Times music editor. After earning a BS from Florida State University, Ryan joined the New Times staff in November 2013 as a web editor.
Contact: Ryan Pfeffer