H'wood Party Girl

She's (almost) always on the list

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Chicago Goes Gaga for Lollapalooza

Amy Winehouse Kevin Mazur/WireImage.com

The Windy City picked up force this weekend when celebs blew into Chicago for Lollapalooza 2007. The music festival attracted the likes of Amy Winehouse, Ben Harper and actor turned deejay Danny Masterson. Though most stars were on their best behavior while performing and partying, some brought their diva 'tude from Los Angeles.

"Ashlee Simpson was wearing the same outfit Friday and Saturday night," one of my Chicago spies tells me. "So, she flat-out refused to take pictures." Though there's no photographic evidence, Jessica's sis supposedly looked like Yoko Ono in all-black attire while cuddling up to boyfriend Pete Wentz in the VIP room of Blender Sessions at the ck IN2U Music Lounge at the Hard Rock Chicago.

Pete Wentz, Ashlee Simpson Paul Warner/WireImage.com

Sunday night, Ashlee finally obliged for the cameras—after much begging, of course—and even managed to force a smile under her stylish fedora.

More happily enjoying the limelight was Kanye West, who surprised guests at Chicago hot spot the Underground with an impromptu performance. I'm told the rapper strolled in around midnight and took a seat next to the club's owner, Billy Dec, before hitting the dance floor. Once his new single "Stronger" streamed through the speakers, Kanye got hold of a wireless mike and belted out the song.

Kanye West Peter Thompson/WireImage.com

Ryan Cabrera, Destiny's Child's Michelle Williams and others got superexcited—though not as zealous as R. Kelly, who motioned Kanye over to join his table after the performance.  Engaging in some "Closet"  chatter perhaps?

Also partying it up Friday night was Hairspray hottie James Marsden. He hung at chic night spot Martini Park with actor buds Josh Hopkins and The Breakup Artists' Greg Bello. While the men munched on Salmon Poppers, Mac & Cheese Stix and Sliders, adoring female fans had to settle for drooling over their own cocktails. I hear James was polite but insisted on saving full-on flirtation for another night. Sorry, Chicago gals. Hopefully next time you'll get your chance.

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