Cityfile: New York's Most Notable and Influential

Spotted | Jennifer Lopez heading into the Bowery Hotel for dinner with Benny Medina ... Bill Cosby walking down East 74th Street ... Drew Barrymore arriving at JFK ... Moby hanging out with friends at the Cooper Square Hotel ... Hugh Jackman taking his daughter for a walk in the West Village ... Justin Timberlake and Jessica Biel on their way to the gym in Tribeca ... Tyra Banks standing around with her crew downtown ... Ne-Yo leaving his hotel in Midtown ... Sarah Jessica Parker walking in the West Village ... Nick Cannon leaving Barneys on Madison Avenue ... Jude Law partying at the Box ... and Jay-Z leaving the Waverly Inn.

• What's Ashley Dupre been up to recently? She's been doing lots of yoga, which she credits with saving her life. And it also introduced her to Russell Simmons, who is now her "mentor" and is making her feel more "liberated." Is that the term they use these days? [P6]
• LiLo and Sam Ronson got in another fight outside a club. This one was caught on tape, however. [TMZ]
• Rumor has it Justin Timberlake and Jessica Biel may be engaged. [NYDN]
• Breaking! George Clooney got drunk at a bar St. Louis last weekend.  [NYDN]More

♦  Lydia Hearst, seen here attending a party last week, doesn't think her family's publishing company should be hosting parties these days. "It's time to work through this crisis, not party through it," she says. [P6]
♦  How are Madonna and Guy Ritchie coping with their split? Madonna has supposedly enrolled in anger management classes at the Kabbalah Center, while Guy has been out with Robert Downey Jr. and Jude Law. [The Sun, People]
♦  Elisabeth Hasselbeck is introducing Sarah Palin at a rally in Florida this weekend. [ET] 
♦  A month after vacationing together in St. Tropez, Jennifer Lopez has asked Benny Medina to come back on as her manager. [Fox411]
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Benny Medina's client roster has been shrinking for quite a while now. In 2003, he was fired by Jennifer Lopez, who later filed suit against the Hollywood power-manager for misappropriating money. He lost another major client last year when Tyra Banks dropped him amid rumors success had gone to his head. ("His perk list is bigger than hers. Everything from private jets and votive candles that the staff has to light before he gets to the set," said one source.) Last month, Usher dumped him; last week, Page Six reported that Benny's biggest remaining star, Mariah Carey, pushed him to the side, reportedly because she caught wind that he was courting former client (and Mariah rival) Jennifer Lopez. Benny denied the rumors and headed off on vacation. And it turns out Mariah wasn't acting crazy after all! More

• Raffaello Follieri is expected to appear in court later this morning and plead guilty to wire fraud and money laundering, a deal that will land him a jail term of 51 to 63 months. [NYP]
• Anne Hathaway says she "spent a week in shock" when she first found out about Raffaello Follieri's arrest. [ET]
• Jeremy Piven, who is decamping to New York for a Broadway role, was overheard saying he wants to take over Sean Avery's old apartment on 19th Street. [P6]
• Star Jones and Al Reynolds hammered out a divorce settlement yesterday. The settlement leaves Al with almost nothing thanks to the "air tight" pre-nup he signed. [P6]
• Wedding alert? Samantha Ronson told partygoers at the Chateau Marmont that "by the end of the year, my love will be Mrs. Ronson." Lindsay says she's looking forward to buying a home "with someone." [The Sun, People]
• Sarah Palin's oldest son Track was addicted to OxyContin? That's what the very reputable National Enquirer says! [Enquirer]

• More on NBC's decision to drop Keith Olbermann and Chris Matthews from covering the election on MSNBC: Olbermann got a raise out of the deal, Matthews didn't, and NBC chief Jeff Immelt may or may not have be behind the move. [P6]
• Howard Stern will auction off a 22-year-old woman's virginity to the highest bidder next week. In the meantime, Beth Ostrosky says she hasn't had had any time to worry about their upcoming wedding because she's jogging 18 miles a day. [R&M, AP]
• Ellen DeGeneres has landed a contract with CoverGirl cosmetics. [P6]
• Jennifer Lopez will be the celebrity judge on the season finale of Project Runway. [Us]
• Scary news: Naomi Campbell says that now that she's had surgery, she can finally have the kids she's always wanted. [People]

• The federal probe into what exactly caused Heath Ledger's death has officially been closed. Which means Mary-Kate Olsen is off the hook, will not have to testify, and can return to her normal (or not-so-normal) life. [NYDN]
• Sienna Miller's friends say she's not a homewrecker, because Balthazar Getty had been separated from his wife for six months before he and Sienna ever hooked up. [Page Six]
• Making it work: Tim Gunn gets paid $30,000 and up for public appearances. [TMZ]