Corrected entry: Dick Dastardly is seemingly unable to win, yet always manages to get in front of all the other racers several times a race. He gets in front to boobytrap the race course, which usually backfires, making him further behind. He then ends up in front again somehow. Since he manages to advance through sections of the racecourse so fast and so many times, it makes no sense to why he can't simply win the race fair and square when he obviously must have the skills/car to do so.
Wacky Races (1968)
1 corrected entry in show generally
Starring: Daws Butler, Don Messick, Janet Waldo, John Stephenson
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Correction: Not really a plot hole. Remember that Dastardly and Muttley are both phenomenally stupid and villainous so it is within their character not to realize that they could win the race honestly.