Jason Derulo clubbed a little too hard. Will Smith's teeth paid the price

Jason Derulo took a shot at "Men in Black" actor Will Smith this weekend, and it didn't end well.

In a potential prank that both stars posted to Instagram on Sunday, the "Swalla" singer appears to chip the movie star's front teeth with a golf club while practicing his swing.

Under the premise of coaching Derulo on his form, Smith sets up a camera to record the moment. "Wait, hold on, don't swing yet," Smith warns, moving toward the ball at the same time Derulo does just that.

Derulo clocks Smith straight in the mouth. The actor crumples to the floor, then crawls toward the camera.

Smith opens wide to reveal two seriously chipped front teeth.

"You ought to put some ice on that," Derulo says.

Tail between his legs (Derulo recently starred in the "Cats" movie as Rum Tum Tugger), the singer tries to slink out of the frame. Smith insists that it's his turn to swing.

As Derulo turns to "just talk about this," Smith nails him with a driver right between the legs.

"And we never saw @jasonderulo again," Smith joked in his Instagram caption.

Derulo posted his own copy of the video, hitting back with, "I don't like this game @willsmith."

While we're not sure if those pearly whites were real, the likely prank echoes back to one Derulo pulled in May. In another Instagram video, he eats corn on the cob off of a spinning drill, yelping to reveal eerily similar chipped front teeth. "Don’t try this 😭😭," he captioned the stunt.

Then again, Derulo's smile looked just fine on Instagram the very next day.

The pair posted a sunny selfie to both of their accounts after the fact, with yet another of Smith's teeth apparently gone MIA. "I gotta stop inviting @jasonderulo over," the movie star wrote. "He's finally embracing his new smile," Derulo responded.