Try to come up with variations of "How much wood would a woodchuck chuck if a woodchuck could chuck wood?"
Examples:
How many boroughs would a burro burrow if a burro could burrow boroughs, bro?
How many yews would youse ewes use if youse ewes could use yews?
How many Sikhs would a sick Sikh sic if a sick Sikh could sic Sikhs? (Answer: six)
I came up with the first one on my own. I came up with a ton more by looking at the homonyms listed on this site.
Examples:
How many boroughs would a burro burrow if a burro could burrow boroughs, bro?
How many yews would youse ewes use if youse ewes could use yews?
How many Sikhs would a sick Sikh sic if a sick Sikh could sic Sikhs? (Answer: six)
I came up with the first one on my own. I came up with a ton more by looking at the homonyms listed on this site.