Jessica Simpson stepped out in NYC wearing a big purple sweater today after spending another night watching her sister Ashlee on Broadway. Ashlee's Chicago performances kicked off this week, but today we're all about looking back at Jessica's year. She certainly weathered some ups and downs — take a trip down memory lane as one of our Biggest Headlines of 2009. We're rooting for Jessica, but it's nice to see that big grin she manages to flash even during some of her toughest moments.
More photos of Jessica out in NYC so read more.