"Courtney Love told me I was the first guy to make lunch boxes fashionable," said Michael Stipe at last Thursday's benefit for hunger-relief organizations the Food Bank for New York City and the Lunchbox Fund. "I wore one onstage in 1980." The R.E.M. frontman reprised his pioneering role for the night's event, held at Chelsea's Wooster Projects gallery. His container, filled with his photographs of friends including Sonic Youth's Kim Gordon and the late River Phoenix, inspired a bidding war between Bono and Coldplay's Chris Martin. Alicia Keys cheered on the U2 lead singer, but Mr. Gwyneth Paltrow came out on top with a winning bid of $20,000. President Bill Clinton's handiwork, meanwhile, fetched $11,000 from the Edge. Lunch box art by the likes of Charlize Theron, Maggie Gyllenhaal, Mike Myers, and Helena Christensen—all of whom lent their starlight to the festivities despite torrential rains—is up for auction through December on eBay (get there via www.thelunchboxauction.org).

Two evenings earlier, Self magazine threw a Courage Night-themed event to relaunch the CFDA's Fashion Targets Breast Cancer initiative. On hand at the publication's Self Center, a temporary spa in Midtown, were Editor-in-Chief Lucy Danziger, Why I Wore Lipstick to My Mastectomy author Geralyn Lucas, and survivor Betsey Johnson. "It's my month to do my thing," said the fashion designer and cartwheel queen. "I added my little diddly-bops to the breast cancer T-shirt and brought back my 'GUYS HEART BJ' tees, the proceeds of which go to a charity. It's Charity City this month in the store!"

Later that night at Cain, Selma Blair showed her love for Montblanc. Dressed by Isaac Mizrahi for her hosting duties, The Fog star stacked four rings from the house's debut jewelry collection on two fingers and wore diamond studs in her ears. She was outdone, though, by über stylist Rachel Zoe, who had hosted a private dinner for the luxury brand at Bottino earlier in the evening. "I'm wearing 12 pieces," she said as John Legend began to perform in the background, "two necklaces, four rings, five bracelets, and a watch." The former fashion editor, whose hectic schedule includes outfitting and touring with starlets like Nicole Richie and Lindsay Lohan, added, "When I started 12 years ago, I never would've thought it'd turn into this. I don't have a day off until December 25."

—Nicole Phelps (The Lunchbox Fund) and Sarah Cristobal (Self and Montblanc)