Fill Out Your Bracket for Round 4 of the PopSugar 100 and Enter To Win Chanel! The races are closer than ever now that we're down to 16 of the hottest and most powerful stars in Hollywood. The tightest race at the moment is one of titanic proportions — environmental activist Leonardo DiCaprio is trailing slightly behind his two time costar and Oscar winner Kate Winslet. Make sure to fill out your ballot with all your picks — and enter to win a $3,000 Chanel bag!