It looks like I'm picking two guys from the "new generation".
Bad Gimmick Made Good = Country Music Star Jeff Jarrett
I think this is a great example of a company getting completely behind a gimmick more so than the wrestler. With all of the bad-ass gimmicks that never got over, to me it's amazing that the gimmick that was best crafted in this era would up be an aspiring Country Music star.
Even though this might sound like I'm over analyzing it, I think what made this gimmick so great, and so believable, was that they actually gave this character "layers". He was given a very logical back story, and from the very beginning he made it very clear at what his goals were in the WWF. He was a guy who wanted to use the WWF to catapult his country music career. It's a very concise and simply goal. He though that through the popularity of the WWF, he was going to somehow get a recording contract by getting his name heard. Makes sense (sort of). He was going to prove to the world that he was the world's greatest wrestler, world's greatest singer, and the world's greatest entertainer...by any means necessary (heel).
Although, I think I've heard stories where Jeff didn't really like the gimmick because he always saw himself as a world champ, straight wrestler, but it was definitely clear the WWF was totally behind this character. They had him shoot DOZENS of vignettes. They gave him a catchy theme song. They gave him very bright, unique wrestling gear, and then through his own charisma, he really made the character his own. Fuck, they even had the guy have a concert during an in your house!...and then eventually gave him a roadie. He was just a really well rounded character. That strut + the light up glasses = gold!
I also loved Tennessee Williams in Jeff's 2nd stint with the character too...and then debra, but that was when Jeff got more "hardcore'. Different character.
Bad Gimmick No One Liked....but Me = The Body Donnas
This is more about my love for the Skip and Sunny tandem, and not the jobber tag team edition with Zip.
This gimmick had all of the makings of a great mid-card heel. Workout freaks who make fun of all of the out of shape losers in the crowd....perfect. But that's not all. This gimmick gave us a dynamic we hadn't seen yet in the WWF, a male/female debuting together, both as heels. Two brand new faces, one in Chris Candido, a fine enough wrestler with a face you absolutely want to punch + a sassy, entertaining, young, and most importantly sexy manager named Sunny. This was also during the time when the WWF were throwing out TONS of really shitty gimmick ideas...just over the top really goofy things (Friar Ferguson!? ew)...so finally we got a normal gimmick that made sense. It was great. It really changed the dynamic of a night.
For me, there's nothing not to like about this set-up. Great theme song, great attire, and the whole thing just looks great. I think that's the most important thing for factions or duos or teams, just overall, how does it look when they come out, and Sunny/Skip looked awesome to me.
But the WWF gave up SO quickly on this and I don't get why. Clearly they saw $$$$ in Sunny, and I know Candido isn't the best talent in the world, but why not use Sunny's popularity to elevate this guy while you can. While I loved the Horowitz angle, I just think it's a shame that that was the extent of the Sunny/Skip angle. Not even a IC title run? Or at least an IC title feud. I could only imagine that a program between Razor Ramon and Sunny being hilarious for a while.
Unfortunately, this was during the era where Vince and the WWF didn't know what the fuck they were doing and let the Kliq run while, nearly taking the company down to the ground (I'm a big anti-HBK guy as you'll soon learn).
Worse off, after the Body Donnas thing ended, it's not as if they put Sunny anywhere else. A few weeks with the Smoking Guns, and then she was left to ring announcing and new t-shirt model duty.... I know her attitude towards the end lead to her downfall, but I think it was all a complete waste.