The problem with utilizing the same characters for multiple decades is eventually you'll have the bright idea to reboot or redesign them. Both are a fine art. A reboot is a bit of house-cleaning, removing what doesn't work and keeping what does. Redesigns run on the fine line of improving on a character's original look, while adding a little something to make a stronger character. Sometimes, it all works out. Other times? Not so much.
Here are some of the best and worst character redesigns and reboots. To soothe the wounds you're about to receive, I'll start with the worst. Think of it like ripping a band-aid off rather quickly.
I'll be honest, I'm doing this one first because I don't wholeheartedly believe in it. I actually have no problem with DmC Dante, even if the delivery of his overall story was crude. I even enjoyed DmC. That said, a ton of people hated new Dante, especially since he supplanted the classic white haired rogue who joined fans in four prior Devil May Cry games. Old Dante knew his life was a joke and loved every minute of it, while new Dante takes the joke too seriously. The white hair and badass red trenchcoat may be gone for now, but they are not forgotten.
Rad Spencer (Bionic Commando)
This is another case of losing the humor in the quest of seriousness. His name is Nathan "Rad" Spencer folks, you don't have to try so hard to make him and his world gritty. The Rad in the original Bionic Commando and its remake Rearmed is a sarcastic redhead who wore sunglasses on his super-secret mission to destroy Hitler lookalike The Leader. Nathan in the reboot is fighting a war against terrorists while looking for his missing wife. The weird thing is, that's supposed to be the same guy ten years apart. I hope I don't age like that.
The Prince (Prince of Persia: The Warrior Within)
In 2003, Ubisoft successfully rebooted Prince of Persia with the Sands of Time, featuring a charismatic Prince in the vein of swashbuckling movie heroes like Robin Hood and the Three Musketeers. How do you follow a great reboot? Ubisoft decided that the answer was more grit and despair. Enter the Warrior Within, which takes the Prince's adventure and replaces it with a relentless flight from an undying enemy. The Prince turned dark and so did his world. The character and the series were not the better for the change. In fact, the Prince of Persia series never quite got the magic back in the two sequels and reboot that followed and Ubisoft has since shelved it.
Bomberman (Bomberman: Act Zero)
Like most of these other poor reboots and redesigns, the problem with Bomberman Act Zero is trying to cram serious themes into characters that don't need them. This game lost the plot in spectacular fashion, turning a family-friendly cartoon into a nightmarish post-apocalyptic cyborg. This is a thing someone greenlit; a committee of people looked at Bomberman: Act Zero and thought it was a good idea. If you ever need an illustration of how little some executives know about what players want, here's the best example ever.
Team Fortress Crew (Team Fortress 2)
When it came time for Valve to update Team Fortress Classic eight years into the original's lifespan, they decided to go a different direction. Instead of the snarling, grimacing faces of the original TF classes, Valve gave the Team Fortress 2 classes a cartoony spin. Each class's silhouette was pushed to be even more distinct, which actually improved the gameplay; being able to tell what you're up against quickly is important in twitch gaming. It also opened the door for the hilarious TF2 movies that Valve has created. What were once just random classes are now actual characters.
Lara Croft (Tomb Raider 2013)
This could've gone horribly wrong - see the Losers up above - but somehow Eidos pulled it off. While Lara Croft in her original incarnations was a soulless sociopath with ample bosom and short pants, the new Lara Croft is a well-realized young woman who will eventually become a soulless sociopath. Big improvement. Plus new Lara wears pants, which is probably a good idea with all the mud, snow, and rock she slides around in. Now if someone could get her a sensible jacket.
Raiden (Metal Gear Solid 4/Metal Gear Solid Rising Revengeance)
Is there anyone who didn't hate the Raiden and Solid Snake bait-and-switch in Metal Gear Solid 2? (Don't answer that, I'm sure there is someone.) Raiden was a decent idea, but the naive soldier thing didn't work out as planned. When Kojima and company brought Raiden back for Metal Gear Solid 4, in his place was a cold, hard, badass cyborg ninja. Even in heels - yes, he has heels - New Raiden was so awesome that players wanted a Raiden-only game, which went on to become Platinum Games' Metal Gear Rising: Revengeance. This is one redesign that actually saved a character for fans.
Link (Legend of Zelda: Wind Waker)
Here's another example where heading in a cartoony direction actually worked out. When Wind Waker was first released, the game was met with some skepticism, especially because fan expectations were tainted by the semi-serious Zelda demo in early GameCube reveals. Years later, after serious entries like Twilight Princess and Skyward Sword, Wind Waker is an more-appreciated game and Toon Link is a well-loved version of the character. Wind Waker Link and his overall world just ended up more fun and expressive than anything that has come before or after.
Honorable Mention: Voldo (Soul series)
Voldo is forever. Every Voldo design is perfect. Every Voldo design tells you everything you need to know about Voldo. Every Voldo is special. He is the best gaming character today. Give love to Voldo. Some call him a demon, but can a demon take up residence in your heart? When the world turns to ash around us, the only thing that will save us is our prayers to Voldo. All hail Voldo.