4 times. 1994 (reject), 1999 (reject), 2000( II, waitlisted, reject) , 2001 (early interview - acceptance.) Better MCAT, better school lest based on package, had a great essay, retook all the classes that had C's or lower, learned from the first interview round, stopped being hung up on being an MD. Applied the first day. DIDN'T GIVE UP.
Best advice someone once gave me when I asked, "What do I do if I get rejected again?". Answer, "You reapply"