[[folder: "''Dick Dastardly cheats because…''" guesses]]
[[WMG: [[DickDastardlyStopsToCheat 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? [[DesignatedVillain 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.
[[WMG: [[DickDastardlyStopsToCheat 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 ''WackyRaces Forever''.
[[WMG: [[DickDastardlyStopsToCheat 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 wont break down.
[[WMG: [[DickDastardlyStopsToCheat Dick Dastardly cheats]] as a form of SelfImposedChallenge.]]
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.
[[WMG: [[DickDastardlyStopsToCheat Dick Dastardly cheats]] to stay [[EnsembleDarkHorse popular with the fans.]] ]]
He's fully aware that the Mean Machine is the best car in the race and he could anytime he felt like it. But he'd rather lose every race and have people be RootingForTheEmpire than win every race and be TheScrappy.
[[folder: Other guesses]]
[[WMG: 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.
[[WMG: The universe itself hates Dick Dastardly.]]
He was stopped for a ''speeding ticket'' at one point.
[[WMG: Dick Dastardly is [[TwistedMetal 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.
[[WMG: The Wacky Races are about as real as ProfessionalWrestling]]
* 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.
[[WMG: The Slag Brothers are from the same universe as ''TheFlintstones'' 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.
[[WMG: Dick Dastardly and Muttley are Time Lords, and the Mean Machine is their TARDIS.]]
How else could they be in both WWI and the 1960's?
* 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 DastardlyWhiplash type is to live for a surprisingly long time.
[[WMG: 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.
[[WMG: 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.
[[WMG: 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 a la 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 UncleGrandpa 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.