The WTF? Moment: In February 2007, a sex tape featuring Ray J and his ex-girlfriend Kim Kardashian leaked out onto the Internet.
Why It Was So Outrageous: It was the sex tapes of all sex tapes. Outside of maybe the Tommy Lee and Pamela Anderson tape, this is the sex tape that’s referenced whenever a celebrity sex tape leaks.
How It Turned Out: Kim accused Ray J of leaking the tape. Ray J (and his mom!) accused Kim of leaking the tape. And, in the meantime, the entire world saw their most intimate moments on their computer screens. But, in the end, this sex tape single-handedly helped Kim launch a successful career and somehow managed to turn Ray J into a celebrity playboy.