John Mayer has been releasing new pop tunes this year and even did something that looked suspiciously like a comeback interview. It didn’t go so well; even though it was for his own Instagram show, he sparked a flurry of 2010-reminiscent headlines by saying he’d slept with “sub-500” women, which was interpreted as around 500 women, which he later clarified was closer to 6. Given that his celebrity reputation was built on the details (often revealed by him) of his time scoring with the ladies, he seems to be struggling in the "Me Too" consciousness of 2018. The point being: As John Mayer makes moves toward some sort of mainstream comeback, we have been wondering: What does a circa-2018 male pop/rock star look like? And can someone like him ever make a comeback if they’ve said, literally, all the worst things in the past? With the help of Billboard editor Joe Lynch, we delve into Mayer’s past, from his irresistible hits like “Your Body Is a Wonderland” to his horrifically racist and sexist interviews to his stellar rock and blues performances. As we dissect whether his musical prowess can ever overcome what he called, in one song, “My Stupid Mouth,” we also examine what makes a good male pop star in 2018, and why his name is...Harry Styles.