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     "Dick Dastardly cheats because…" guesses 

Dick Dastardly cheats because... he's supposed to.
All cars, crews, and drivers in the race have a gimmick. Otherwise, it wouldn't be wacky enough. It's in the rules.

What's Dick's gimmick? Being the villain, of course.

He's allowed to take shortcuts and set up traps because he's the bad guy. If he won without trying to sabotage others, then he would be disqualified for cheating.

  • For the record, Peter Perfect has the gimmick of being an almost-normal racer. He's a presumptuous blowhard; aside from that and the stretching limbs/etc, his car is an actual racing car and his behavior is mostly that of an actual racer. He is permitted this because it makes the other racers look wackier.
  • This theory makes sense if you think of Wacky Races as having been staged in-universe like professional wrestling. All of the drivers are engaging in Kayfabe, and Dastardly is a firm Heel who's supposed to lose. The actor playing Dick knows he can never win, and he's okay with that. He just wants to put on a good show, and boy does he ever.

Dick Dastardly cheats because... he's cursed.
Basically, he and Muttley are immortal, as long as they don't play by the rules, he gets to keep living. But the curse also stipulates he will forever humiliate himself. He cheats out of fear that if he does not, he'll die, though this is more subconscious. That's why he's been alive since World War I and would have appeared in Wacky Races Forever.

Dick Dastardly cheats because... The Mean Machine can't maintain a winning pace.
The Mean Machine seems to pass all the other divers multiple times during a race. Perhaps if it were to go that fast the whole race it would break down. So Dick stops to slow his opponents down so he can go at a pace at which the mean machine won't break down.

He must be a racer good enough that simply winning will gain him no satisfaction. He regularly gets far ahead of everyone else due to his skill, so he feels there's no challenge if the other racers have no chance of beating him. The cheating, which requires him to stop in one place for long periods, allows the other racers time to catch up and make the race more interesting, and even temporarily grants the other competitors an advantage.

He's fully aware that the Mean Machine is the best car in the race and he could win anytime he felt like it. But he'd rather lose every race and have people be Rooting for the Empire than win every race and be The Scrappy.

Dick Dastardly cheats because he knows it will cost him the race and he's bet against himself using aliases
In the way that truly counts, he's a winner alright.

Dick Dastardly cheats because he believes he can't win any other way.
Sure, we know that logically if he just drove and drove and drove, he probably could win a race or two simply because his car is the fastest and he has the skill to drive it. But he doesn't know that. He's always trying to get the other drivers to drop out of the race completely because, for some reason, he doesn't think he can actually beat them fairly without cheating. Is he trying to ensure his chances of winning or does he just lack confidence in his own skills? We may never know...

     Other guesses 

Red Max is the son of the World War I era Dick Dastardly.
He flies a WWI-era biplane which he has trouble getting off the ground, much less starting, much like the Vulture Squadron. He doesn't cheat, but he has used artillery to his advantage.
  • So now the reboot has Dick-the-racer as Dick-the-pigeon-chaser's grandson, are we to conclude we're heading for a Luke, I Am Your Father moment?

The universe itself hates Dick Dastardly.
He was stopped for a speeding ticket at one point.

There is an unofficial Code of Honor
As mentioned on the main page, everybody cheats in some way, yet only Dick Dastardly is called out on it. But the thing is, there are two things which set him apart: a) he is very malicious and b) he stops to do it. Everybody else cheats, yes, but they never gloat or do it just to hurt others. And in fact, other racers will also often help each other. And second, other racers seem to use almost exclusively their cars' abilities - meaning that this sort of cheating could actually be allowed, either unofficially or maybe even officially. Dick Dastardly is dastardly not because he is a cheater, but because he is breaking the rules of the game, as well as being outright malicious.

Dick Dastardly is Sweet Tooth's grandfather.
My main basis for this theory is that both have a tendency to cause massive destruction in weaponized cars and their both villains, except Needles is more competent.

The Wacky Races are about as real as Professional Wrestling.
  • That's why Dick never wins—he's the bad guy wrestler equivalent. He's supposed to lose. Moreover, his constantly setting traps may never take out all the other racers, but often does change who's in what position, making it easier for the person who's supposed to win the race to, well, win the race.

The Slag Brothers are from the same universe as The Flintstones and never appeared on that show.
It makes sense because they're cavemen.
  • Captain Caveman was a Slag expy, and he appeared on the 1980 and 1986 Flintstones shows.

Dick Dastardly and Muttley are Time Lords, and the Mean Machine is their TARDIS.
How else could they be in both WWI and the 1960s?
  • Time period is roughly ambiguous and I was given a point Mr. Burns has lived through both those things and then some. Dick and Muttley might be surprisingly old. The power of the Dastardly Whiplash type is to live for a surprisingly long time.

The races are a sort of reality show.
The fourth wall breaks are done by people speaking into the cameras, cameras that are filming them race in a bizarre sporting event.

Dick Dastardly is a Ghost Rider.
After selling his soul to save his beloved companion Muttley, he's doomed to race for all eternity, with the promise that winning will set him free. The resurrected Muttlety was part of the faustian bargain, turns out the whole coming back to life thing turned him into sadist who delights in seeing his master fail. If he ever escaped from Hell, Dastardly would spend his life riding around the desert in the Mean Machine with a flaming skull for a head and Muttley as his skinless dog companion.

Thoughts on what the reboot could alter.
Excluding the obvious likely change of voice actors and the change of technology there is a lot which could happen as we wait or more details this year. Will the character designs look à la Wacky Races Forever or look like how it was in the original cartoon but with an animation boost similar to Dick and Muttley's cameo in the Uncle Grandpa episode "Uncle Grandpa Retires"? Will some characters be removed, which leads to the introduction of new racers? These are all very important questions to joke and might be revealed as the truth.
  • For one thing, I hope we get an announcer back. The lack of Colm N. Tator in the pilot of Wacky Races Forever is the only complaint I had that seems good to mention.
  • Although the original cartoon's episode plots of simply racing in an area, Dick trying and failing at gaining first place leading to laughs from his canine companion, and all wackiness in-between could easily fit Cartoon Network's current single 11-minute episode release style, a bit more could be done in how entertainment has changed in this new age. Instead of a simple race the track there could be expansion and development on the racers' personalities, backgrounds, and reasons they decided to become Wacky Racers to begin with. Just because the title focuses on the races doesn't mean everything has to be on wheels 24/7, though that will be a basic in most episodes.
  • Boomerang’s 2017 new show preview trailer showed off some pieces of the cartoon.In looks it more-or-less resembles the original work but with a more modern animation style with brighter colors and no black outlines. Red is no longer one of Dick’s colors as his outfit now consists of various shades of purple with hints of gold buttons (His coat also no longer goes down to the top of his boots). Muttley’s outfit may or may not be inspired by Dastardly and Muttley (As in he might be wearing a scarf and hat with goggles instead of just a collar). It also looks like there might be new racers, which at least one seems to be another female thus far meaning Penelope is no longer the only female racer.

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