No. 1
It's a tie between the Monopoly man and Ed. Pinaud Clubman

No. 2
Joe Camel

No. 3
Quaker Oats guy

No. 4
Capitan Crunch

No. 5
Burger King's The King
Debonair Magazine just listed the top 10 best dressed advertising icons of 2008. Sadly The Jolly Green Giant only made it in at number 8, missing my top 5 cut. For the full run down click here: http://www.debonairmag.com/top_10_best_dressed_advertising_icons