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Mega Pidgeot as a to tribute to the Golden Bird he supposedly worships
Gastrodon to use its Storm Drain ability so it can collect Gypsy Tears. Also for filling wells.
Pignite to strike fear into the hearts of Jews
Kriketune for its musical abilities
I honestly don't see him having more than 4 pokemon.
Ali G would simply have 4 Scrafties
Bruno would most likely use 3 Furfrou in different fashion styles, all in fur cuts he invented himself, and an extremely homo Gallade to help him cut the Furfrou's fur.