October’s Very Awkward: A Gallery Of Drizzy Drake’s Goofiest “WTF” Pictures

- By Bossip Staff Categories: Caption This, Caught Looking Busted, For the Ladies


Drake’s not your average hardcore rapper. In fact, he’s probably the most sensitive rapper to ever put out an album. He’s not afraid to share his emotions. While we can commend his bravery, we can still make fun of his most buttery soft, pansy a$$ pictures.

Join in on the fun and post links to your own funny Drake picture!

drake hugging wayne

We posted this picture last week from Drizzy’s OVO concert. We’ve definitely noticed his…unique…relationship with Wayne. We’ve accepted it, but this hug just made everyone uncomfortable. That’s too much man flesh touching.

drake and bieber

Drake loves Bieber. Bieber loves Drake. We’d say they had a bromance but Bieber’s age would make it illegal. So…they just have a really awkward relationship where they hug and smile a lot.


Bieber, blink once if you need us to call the authorities. Blink twice if you need a stun gun. Like we said, Drizzy loves hugging and Bieber is his humber one huggee.

old school drake

This is the face of the highest grossing new artist in Hip-Hop. Doesn’t he just exude a suave bada$$ demeanor? No? Well, he’ll grow into a smooth, cool MC. Or at least one that the ladies love.


Take your bets as to what’s playing that makes Drake dance like that with his glass of Moscato up to the high heavens. “It’s Raining Men”? “Girls Just Wanna Have Fun”? Whatever it is, Drake’s got that, “Girl, this is my JAM!” look on his face.

drake rihanna

We all know about Drake and Rih Rih. But here, Drizzy’s got the “back off, because I’m chopping this Red Hair to smithereens…right after I trim the split ends.


Here’s another picture from Drake’s childhood where he looks like a mixed version of Tiny Tim. We hope this is a costume and he didn’t rock this outfit to school or anything. But we wouldn’t be surprised if he still had this in the closet.

drake happy

Here’s another image of Drake and Wayne. This time, Drizzy is holding his crotch in delight watching Weezy rap on stage. He’s giddy like a tiny schoolgirl. How sweet.


He looks so happy, like he’s dancing on a cloud and snuggling with Care Bears. His favorite Lady Gaga track is playing and he’s snapping his fingers. Maybe he’s even whipping his hair back and forth.

j cole drake

Poor J Cole. He got straight bombarded with this monster hug from Drake. If you could see Cole’s face, you’d probably just see fear and despair. No one is safe from a Drake hug.



    The ni66a looks like a retarded alien! E.T. phone home!

  • Christielove1468

    Awwww,these pics are sweet!.Drake probably was born happy and he loves life.

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