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.
The WTF? Moment: Shortly after the sex tape leaked, Ray J tried to attend a pre-Grammy Awards party that was being hosted by Kim Kardashian, who reportedly had security ask Ray to leave.
Why It Was So Outrageous: Ray J was obviously not happy with leaving well enough alone. Rather than keep his distance from Kim for a couple of months to let her cool off, he tried to attend a party she was hosting just days after the tape leaked.
How It Turned Out: Ray J and Kim reportedly keep in contact today, so we're guessing she's over the he-said, she-said that came along with the sex tape being released. But at the time, this put a real strain on Ray J and Kim's relationship and almost turned the incident with the tape leaking into a very sticky situation.
The WTF? Moment: In December 2007, Ray J tried to use the publicity generated by his sex tape with Kim Kardashian to publicize his new mixtape, Ray J Unkut—which featured this tacky animated cover.
Why It Was So Outrageous: Just look at it! It's completely ridiculous, tasteless, and, well, it just wasn't a good idea for Ray J to abuse the publicity he got from the tape so blatantly.
How It Turned Out: No one downloaded this tape. No, really: No one. Okay, okay, so we're sure a few of you out there downloaded it, but even with a DJ Kay Slay cosign, most people saw this for the blatant publicity stunt that it was.
The WTF? Moment: In March 2009, Tila Tequila took to her blog to reveal that she was dating Ray J. He later sent her a tweet calling her "future wifey" that seemed to confirm what she had said.
Why It Was So Outrageous: Ray J and...Tila? Say it ain't so. What more can we say?
How It Turned Out: We're not really sure whether or not Ray J was actually dating Tila, but he had us scared for a second. Fortunately, we're pretty sure these two either called it quits quickly or never really got off the ground as a couple. Either way, we're just glad they're not still together today.
The WTF? Moment: In February 2007, Ray J and Whitney Houston were spotted together at NBA All-Star Weekend in Las Vegas and rumors that they were dating started flaring up.
Why It Was So Outrageous: Ray J was 25 at the time, and Whitney was 44. That's all well and good, but something just seemed really off about these two as a couple. It was almost like we couldn't believe what was taking place right before our very own eyes every time we saw them out together.
How It Turned Out: Ray J revealed that he and Whitney never actually dated in 2010, but there was obviously something going on between them. Lucky for us, it seems to have fizzled out because they haven't been spotted together anytime recently.
The WTF? Moment: In February 2009, Ray J starred on a reality show called For the Love of Ray J, which featured him giving female contestants silly nicknames. After two seasons, it yielded zero marriage prospects.
Why It Was So Outrageous: Everything about this show was ridiculous. It made for good TV, but did anyone really think that Ray J was looking to settle down with a chick he found on a reality show? Not likely.
How It Turned Out: As a result of the success of For the Love of Ray J, VH1 eventually picked up a spin-off series called Family Business, which also featured Ray J's sister Brandy and other members of his family. It wasn't exactly the best show we've ever seen, but it was a hell of a lot less cheesy than For the Love was.
The WTF? Moment: In June 2010, Ray J got himself involved in the Lil Kim/Nicki Minaj beef by helping Kim call Nicki out during a concert.
Why It Was So Outrageous: Ray J and Kim have always had a bit of a mysterious relationship—as in, why do they seem to hang around together so much?—and that was never more evident than it was last year when Ray J interjected himself in the middle of a beef that he had no business being involved in.
How It Turned Out: Nicki and Kim still hate one another and Nicki Minaj probably won't ever do a song with Ray J. The world is a better place because of it.
The WTF? Moment: In January 2010, a Ray J concert was featured on a video produced by DJ Kay Slay and Straight Stuntin' magazine that featured him throwing up gang signs on stage and wearing all red.
Why It Was So Outrageous: Hold up, was that Brandy's brother throwing up gang sings? The one who used to be on Moesha? The one who sang "One Wish"? The one...oh, you get the point.
How It Turned Out: We're not sure exactly who Ray J is down with but, um, yeah. It was definitely a little bit strange seeing him up on stage acting like the biggest thug ever considering his background.
The WTF? Moment: In August 2011—on Kim Kardashian's wedding day—Ray J allegedly sent her a text that read, "And to think you really have me to thank for all this :-)"
Why It Was So Outrageous: You could make the argument that Ray J is the reason Kim has transformed into one of the biggest celebrities in the country. But, if he really did send this text message to her, it's no wonder she's marrying some other guy and not him.
How It Turned Out: Ray J doesn't deny that he sent a text message to Kim. He just won't reveal what he said to her. As a result, we have no choice but to think that he did say this or something along the lines of this. Not cool, bro.
The WTF? Moment: Earlier this month, Ray J approached Kim Kardashian's husband Kris Humphries on a plane to congratulate him on putting a ring on his ex-girlfriend's finger.
Why It Was So Outrageous: LMAO. Are you kidding us with this one? What are the odds of Kim's husband and Kim's ex-boyfriend meeting up—on a plane of all places!—and why did Ray J have to make it awkward by walking up and trying to talk to him?
How It Turned Out: After Humphries initially tried to say that he didn't know who Ray J was, he gave in and said thank you for the well wishes. And once again, all we could think was "WTF?"