The Dudley Boys were leaving ECW for the WWE in 1999, on their last appearance on ECW on TNN, they challenged Tag Champs Balls Mahoney and Little Spike Dudley to one last title match. The Dudley's won the match, and were now 8 time ECW tag champions. This was a nightmare since the Dudleys could not walk out of the company with the belts, and made clear that that was they're intention. That they would now leave with the belts, and place them on Vince McMahon's desk. They called out anyone in the company to try and take the belts back, and Tommy Dreamer answered the call. Paul Heyman then made a rare public appearance pleading with Dreamer not to go through with it due to the fact he was working with two herniated discs in his back, and if he fought The Dudleys alone, they would destroy him. The Dudley's goaded Dreamer and played on his sense of loyalty talking about how they would disgrace the belts, while Paul E told Tommy "I don't care! I don't care! Just please don't do this!" But Dreamer's loyalty won out. He hit the ring and attacked the Dudleys, Dreamer was quickly knocked out and in a surprise move no one saw coming, Raven snuck in the back door and took out D-Von, Evenflow DDT'ed Bubba, and covered him, making Tommy and Raven new tag team champions. When Dreamer came too, it was a nightmare visual, Raven had returned, and as he handed Tommy his half of the tag titles, Dreamer sank to his knees...Tommy Dreamer had won his first title...but had to share it, with his most hated enemy.
Raven did a series of vignettes in which he talked about how this was part of a master plan to destroy Dreamer, that Dreamer would have to share the titles with Raven, and Raven would not allow Dreamer to lose them. Tommy did a series of vignettes also, doing the only thing he could in that situation...pleading with Raven to let the past go, and to become a true partner to Dreamer "Do the right thing Raven, do the right thing" became Dreamer's mantra. Slowly but surely, Raven began to trust Dreamer, and they became a pretty good tag team, Raven was "doing the right thing", then at the beginning of November...another man made his shocking return. The Sandman had come home to ECW, and he hadn't forgotten a damn thing Raven had done to him, and Raven hadn't forgotten about The Sandman. Dreamer was friends with The Sandman, and now had a friendship with Raven, he was caught in the middle, and trying to mend fences. It wouldn't work, The Sandman beat Raven up after the November to Remember PPV six man match that all three men were involved in. Raven's fragile psyche was in turmoil as he was seen on ECW's weekly TV show on TNN muttering "I did the right thing Tommy! Why'd you let the drunk beat me?" over and over...then abruptly changing his words, to what was REALLY torturing him, and had tortured him for so many years: "I did the right thing mommy! Why'd you let the drunk beat me?" Raven and Dreamer lost the tag titles shortly thereafter to the Impact Players, Lance Storm and Justin Credible. Won them back, then lost them again. Raven then turned on Dreamer and took Francine with him. Raven then began teaming with Mike Awesome, with "The Sinister Minister" Jim Mitchell hovering around and trying to recruit Raven. It never really panned out as Raven had only signed a one year deal with ECW, and because of personal problems he was having with alcohol at the time, was not putting forth his best effort, and was using the company as a stepping stone to rehabbing, and going to WWE. It was a sore spot between Raven and Paul Heyman until they both came to work for Vince, and reportedly had everything out, and came to an understanding (basically, Raven apologized for his behavior, and for using the man who had given him so much).
Raven's time in WWE was pretty uneventful. Like in WCW, management just didn't know what to do with the character. He won a tag championship with Tazz (my god, I could go on for so long about how they wasted a golden oppurtunity with that duo), and was primarily working as a Hardcore champion or contender for the belt (he is near the top of my all time best hardcore champions list). There was an angle in which he had a woman dressed as a ninja helping him win matches, but after it was revealed that Tori was the ninja, the angle was abruptly dropped, and Raven changed his look with no explanation. He bounced around as a job guy pretty much, gaining one last Hardcore title reign to bring the belt to RAW just after the brand extension, and then promptly lost it only four days after winning it to Bubba Ray Dudley. From there, Raven wasn't used much. He would have one last match with Tommy Dreamer, in a "loser leaves RAW match", Raven lost, and was then relegated to Heat. Raven claimed this wasn't neccessarily a bad thing, because he would make Heat his "personal playground" but nothing ever came of it (according to Raven, he had pitched an angle to Vince, Vince had liked it, and told Raven they would pull the trigger on it and do it. But that because Raven did not get along with Lead RAW Writer Brian Gerwitz, the angle was never done, even though it had Vince's approval). Raven worked on Heat for a a couple more months, and then received his release.
He floated on the indies for awhile (making good money as he is a favorite of the net, and the indy fans), until NWA: TNA opened and Raven got a deal there. Now would be the point that a TNA fan should pick up because I really don't watch TNA, I only know that he shaved his head or something (WTF?!) and received a shot or two at Jarrett's title.
This by the way, is not swiped from any site, I sat here for about two hours racking my brain and typing all this up myself, so hopefully a few of you will take the time to read it, since I worked so hard on it.