Yikes. Justin Bieber and Chris Brown posed for arguably the most awkward photo at Coachella so far (and yes, we're including the whole Madonna/Drake makeout sesh), with the controversial singer pretending to punch Justin in the face for the camera.

While the two have long been friends and collaborators, we guarantee that the picture would be a lot more innocent if not for Chris Brown's checkered and violent past, which includes his infamous and brutal assault on Rihanna in 2009 and multiple outbursts of violence since.

In 2009, Brown assaulted his then-girlfriend Rihanna after a pre-Grammys party, punching her so badly the "Umbrella" singer's face was bloodied and swollen. Since the domestic violence incident, Brown has also been sued for beating up a fan in a Washington, D.C. parking lot and for engaging in another parking lot confrontation with singer Frank Ocean. He has also served time in both rehab and jail for his transgressions. In fact, it was just four weeks ago that Chris Brown's probation — stemming from the Rihanna assault six years ago — finally ended. So yeah, we're going to hazard a guess that it's probably not too wise to pose for a photo opp in which you're pretending to assault someone, long time friend or not.

You can see the ill-timed photo of Chris Brown and Justin Bieber above.

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