In the 1970s, San Francisco painting contractor Bill Holland discovered he could save money on business cards by listing himself as Zachary Zzzra in the local telephone directory and telling potential customers to find his number at the end of the book.
This worked well until he was displaced by a Zelda Zzzwramp. He changed his name to Zachary Zzzzra but was overtaken by Vladimir Zzzzzzabakov. So in 1979 he pulled out all stops and became Zachary Zzzzzzzzzra.
Victory brought its trials. “People making illegal calls from phone booths look up the last name in the book and charge them to me,” he admitted to Time. “I don’t pay a damn one of them.”
06/17/2024 UPDATE: Reader Nick Semanko adds that in 1964 two Rhode Island politicians, Raphael R. Russo and Mario Russillo, changed their names to aRusso and aRussillo so that they could appear at the top (technically the left) of the ballot. aRussillo won and aRusso lost.
Four years later the two faced one another for the position of town administrator of Johnston. aRussillo added another a to his name (becoming aaRussillo) and won, though aRusso eventually succeeded him. aaRussillo dropped the extra letters from his name in 1995, but aRusso kept his to his death in 1999. (Thanks, Nick.)