1776 - 1837
Tied with Thomas Cole in his initial Round 1 outing, in September 2012.
Lost to Ansel Adams in his second try at Round 1.
Lambasted Lithuanian sculptor Jacques Lipchitz in First Round Elimination.
Fra Filippo Lippi
1406ish - 1469
Beat his own son in Round 1.
Lost a shocker to El Lissitzky in Round 2.
Vote for the artist of your choice in the comments, or any other way that works for you. Commentary and links to additional work are welcome. Polls open for at least one month past posting, but likely much longer.