Justin Timberlake is one of Hollywood’s most beloved musicians and celebrated actors, not to mention a favorite on Saturday Night Live. He also may or may not be super shady, depending on which tabloid you actually want to believe. From wardrobe malfunctions to awkward song titles, here are all the times JT has been out of sync with the public.

He dissed football at super bowl press conference

Open mouth; insert foot. At a press conference leading up to Timberlake’s 2018 Super Bowl Halftime performance, he actually dissed the NFL. Seriously.

When asked if his son, Silas, would ever play football someday, Timberlake replied, “Uh, he will never play football. No, no.” 

To be fair, a lot of reports have come out recently about the negative effects of football (specifically, concussions) on players’ brains, but this was probably the worst possible forum for Timberlake to make this particular statement.

He seemed to realize his error and attempt to back-pedal from the remark, telling press, “I mean, yeah, it’s kind of like that thing where my main objective is that he become a great person, and if he wants to get into the arts or sports, then yeah, I would fully support that. I think I can hopefully offer him some advice on what to do and what not to do, so yeah, but right now we’re working on our manners. That’s a big deal in our house right now. It’s like, one thing at a time.”

He is been accused of cheating on Jessica Biel

While Timberlake and actress Jessica Biel are happily married with a son, it’s no secret that their road to the alter was filled with dramatic headlines, breakups and, perhaps worst of all, multiple allegations of cheating. Arguably the biggest allegation came in October 2010, when Us Weekly reported that Timberlake had engaged in a three-day fling with actress Olivia Munn after meeting her at an event for MySpace. (Remember that?) Timberlake vehemently denied the report.

Still, rumors of infidelity continued to plague their relationship. On the heels of their breakup in 2011, Timberlake’s Friends with Benefits (2011) co-star Mila Kunis was accused of being the catalyst. Even after he and Biel got back together later that year, Us Weekly soon reported that Timberlake had visited Scarlett Johansson’s apartment after flirting with her all night.

Uh. All’s well that end’s well?