When people think of Will Smith, “cool” and “confident” usually come to mind. Who knew the guy would be insecure about his wife having a male friend? Leave it to Smith to stun us.

Jada Pinkett Smith’s relationship with the late Tupac Shakur made her hubby uneasy, and he’s not ashamed to say it.

No Tolerance For Tupac

As reported by Page Six, “Radio host Charlamagne tha God asked Smith, 51, on ‘The Breakfast Club’ on Monday whether he was ever jealous of Shakur, to which the ‘Bad Boys for Life’ star responded, ‘F—k yeah.’” Blunt and honest, Smith didn’t hide his feelings.

Smith went on to say he regrets how he felt because he missed out on the opportunity to get to know the guy his wife was so fond of.

“Just Friends”

Jada met Tupac when they were students and their friendship lasted. They were always “just friends,” although one time they attempted to cross the line, and the kiss was “disgusting,” something she shared with Howard Stern.

Too Little, Too Late

Too bad Smith couldn’t get over his insecurities before Tupac’s untimely passing.

Of course, we’ll never know, but if Tupac were still alive today, maybe Smith would have come to his senses by now and loosened up to let Tupac in.