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Ray J has a lot more to be regretful for than that sex tape with Kim Kardashian. He’s been acting a mess for years now, Kim K was just the tip of the iceberg.

Since “Brandy’s Brother” stepped out of her shadow and into his own spotlight, Willie Norwood Jr., hasn’t stopped keeping us entertained. Depending on what he’s promoting, you’ll see his face splattered across TMZ more often than usual. To that end, Ray is a master marketer. He knows how to get people’s attention.

To give a little perspective, Ray J’s first album — Everything You Want — came out in 1997. That was almost 20 years ago. This dude has been at this for a while.

Along the way he’s made a lot of weird moves. There’s no telling if his career would be the same without the controversial stuff, take a look back at “10 Other Things Ray J Should Regret” in the gallery.

Photo: Instagram

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