POPSUGAR Celebrity

Biggest Headline of 2009: Jessica Simpson's Ups and Downs

Dec 2 2009 - 10:30am

Jessica kicked off 2009 with a pair of questionable jeans [1] that brought up a serious debate over her weight. Ashlee spoke up [2] defending her sister, and even the President added his two cents [3] on the issue. Jessica kept her chin high, performing in her famous daisy dukes [4], even if she sometimes forgot the words to her songs [5]. By mid-February things were looking up for Jess as she and Tony Romo [6] spent Valentine's Day together in NYC [7] before a romantic getaway [8] in March. The weight debate was put to rest for a bit as Jess showed off her bikini body [9] while vacationing in Mexico. The Vanity Fair cover girl [10] decided to put her experience of being under the microscope to good use and signed on to host a new show inspired by her experience called The Price of Beauty [11].

Jessica spent Fourth of July weekend singing the national anthem [12] at a golf tournament where Tony played. The good times came to an end mid-July as news broke of Jessica's split with Tony [13] right before her 29th birthday. Simpson returned to a familiar post-breakup routine, hitting the gym daily [14] as everyone speculated about her broken heart. Jessica also weathered the release of her Glamour magazine cover — written before the breakup — in which she spoke openly about their relationship [15] but acknowledged it might not last forever. Jess was soon off on trips to Japan [16] and Paris [17] for her show. On her return from a trip to Brazil [18], tragedy struck when Jessica's beloved dog Daisy was snatched up by a coyote [19] as she watched in horror. The search for Daisy continued for days until Jessica began the healing process with a trip to Paris for Fashion Week [20] with Ken Paves.

Jess seemed to be in better spirits as time moved forward and she headed to Vegas for Ashlee's 25th birthday party [21] in mid-October. Jessica's global tour wasn't over yet: she headed to Morocco [22] and India [23] before landing back in the States to celebrate Bronx's first birthday [24] and Ashlee's Broadway debut [25]. Through it all, Jessica has kept her head held high and that famous smile bright — we wish all the best for Jessica in 2010!

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