I once hit jackpot on a slot machine (actually my girlfriend did, but I was totally standing *right there*). Nickel slots; $60. We were rolling in nickels.
In case you are not satisfied with the amount of things you win in lotteries, the following approach (mentioned in yesterdays news) may help you:
automatic participation in twitter contests (using a script).
Of course you would write your own Perl-script for doing this tasks ;-)