Santa Anna's whole career was pretty bizarre. How does anyone serve as President on 11 non-consecutive occasions?
In that vein, the political career of Norodom Sihanouk surely counts. Twice King, thrice President, and ten times Prime Minister (if Wikipedia is anything to go by), not to mention inveterate ally of the Eastern Bloc and even the Khmer Rouge (!), who spent much of his final retirement dividing his time between houses in Beijing and Pyongyang (!!!).
But one probably cannot beat Emperor Bokassa I in terms of pure surreality.