Cityfile: New York's Most Notable and Influential

♦  Although her life looks like it's finally back on track, a new documentary suggests Britney Spears thinks her new life is like prison and lacks "excitement" or "passion." Hopefully she'll be in a better mood in two weeks when she makes an appearance at the Rockefeller Center tree lighting ceremony. [The Sun, OK!]
♦  Could Anna Wintour be planning to retire? Page Six says the Vogue editor is thinking about leaving the mag once her contract is up, and she's even been recommending possible replacements to Si Newhouse. [P6]
♦  Kiefer Sutherland may be planning to move to NYC so he can be closer to his girlfriend, Allure style director Siobhan Bonnouvrier. [Daily Star]
♦  Madonna is reportedly making $10 million to appear in her new Louis Vuitton ad campaign. [P6]More

Lucky hosted its fifth annual "Lucky Shops" last night inside the Metropolitan Pavilion. Lucky editor Kim France and publisher Gina Sanders welcomed Leighton Meester, Jessica Szohr, Georgina Chapman, Katrina Bowden, Alexandra Richards, Charlotte Ronson, Thalia, Beverly Johnson, Ginny Barber, and Michaela McManus, who all did a little shopping to benefit the Robin Hood Foundation. [The Daily, PMc, Wireimage] More

♦  A long list of celebs have been involved in a last-minute effort to get out the vote for Obama, including Oprah, Diddy, Sarah Jessica Parker, Matthew Broderick, Edie Falco, John McEnroe, Mary J. Blige, Russell Simmons, Beyonce, and Jay-Z. In the elderly celebrity writer department, Vanity Fair's Dominick Dunne says he postponed surgery so he could vote today. [R&M, Politico]
♦  Ivana Trump has been calling Marius Rusovici, the 23-year-old Belgian she's been hanging out with, "her boyfriend," although it may just be a plot to make Rossano Rubicondi jealous. Or stir up some press. Or both. [NYDN]
♦  David Duchovny and Tea Leoni were spotted holding hands while their kids went trick-or-treating on the Upper East Side last Friday, which may or may not mean they're getting back together. [P6]
♦  Sumner Redstone's ex-wife, Paula Fortunato, is still living in his Beverly Hills mansion. But he may have already reunited with his ex-girlfriend, Manuela Herzer. [P6] More

♦  You didn't expect to hear that Lydia Hearst actually wrote that column in Page Six magazine by herself, did you? In response to Hearst's accusation that Page Six fabricated her latest column—the one in which she bashed her family's publishing company—the mag now says that Hearst's writing process involved being interviewed by a reporter who then "put her thoughts into cohesive paragraphs." And they have the emails to prove Lydia's trash talk. [P6]
♦  Madonna is reportedly under pressure from the leaders of Kabbalah to reach a divorce settlement quickly, lest the mess cast a negative light on their freaky cult. Guy Ritchie, however, isn't making it any easier now that he's apparently rejected Madge's latest £20 million offer. [Daily Mail, ThisIsLondon]
♦  Michael Phelps got paid $100,000 to swim around at a pool party thrown by a TV network chief's wife. [P6]
♦  It's a match made in heaven: Jamie-Lynn Sigler and Jerry Ferrara, who plays Turtle on Entourage, are dating. [R&M]More

Spotted | Jay-Z and Beyonce leaving 1OAK ... Michael Phelps leaving MTV studios in Times Square ... Juliette Lewis using an ATM in SoHo ... Katie Holmes leaving her apartment building on East 13th ... Uma Thurman shopping in the Village ... Brooke Shields, Kim Raver, and Lindsay Price filming scenes for Lipstick Jungle in the West Village ... Carrie Underwood posing with her wax figure at Madam Tussauds on 42nd Street ... Agyness Deyn and Albert Hammond Jr. walking with a friend ... Donatella Versace leaving the Chanel Mobile Art afterparty at the Waverly Inn ... Kate Bosworth outside the same party ... and Madonna getting out of a helicopter while carrying son David.

Jay-Z Breaks It Down | The Obama campaign posted a little instructional video featuring Jay-Z yesterday. Who knew Jay was so familiar with voter registration laws? We look forward to his explanation of how the electoral college works next week. In the meantime, the video is below. More

♦  Are Madonna and Guy Ritchie really divorcing? It might be another rumor or really a Sun exclusive, but the British tabloid says they plan to announce the split as soon as today. [The Sun]
♦  Christie Brinkley is suing Peter Cook for violating the couple's confidentiality agreement by talking about their relationship on 20/20. [NYP]
♦  The "mystery illness" that's caused Janet Jackson to cancel tour dates is supposedly a vestibular migraine, which "induces the sensation of vertigo." The good news is that now she's apparently cured. [ET]
♦  Raffaello Follieri's lawyers yesterday asked a judge to "go easy" on Raffaello in exchange for his quick return to Italy where he'll "never be heard from again." Ha! [NYDN]
♦  The 40-year-old CEO of a company called Future Tech Enterprise on Long Island is actually paying $20,000 to box Michael Lohan. And Stephen Baldwin is now planning to serve as the match judge. [Newsday via NYO]
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♦  Not only did Jennifer Lopez and Marc Anthony renew their vows at 3:15 a.m. in Las Vegas on Sunday, they did it in a joint ceremony with Mets outfielder Carlos Beltran and his wife Jessica.  [E!, People]
♦  Lindsay Lohan and Samantha Ronson tell friends they're planning on dressing up as Todd and Sarah Palin for Halloween. [NYDN]
♦  Jay-Z couldn't get any London clubs to pay his $50,000 appearance fee this weekend. [This London Blog via E!]
♦  Is Suri Cruise lonely and sad because has no friends her own age? [P6]More

♦  Michael Phelps is telling people he's single even though he's actually dating Miss California runner-up Nicole Johnson. [R&M]
♦  Peter Cook's interview with Barbara Walters airs on Friday, but Christie Brinkley's lawyers now say he violated a confidentiality agreement by speaking with the network. [OK!, ABC News]
♦  Hugh Hefner says his relationship with Holly Madison began to crumble six months ago when they found out his sperm count was too low to father any kids. Also, he's already auditioning new girlfriends. [E!]
♦  Anna Wintour's latest celebrity obsession? Gerard Butler. [P6]More

Spotted | John Mayer leaving a Krav Maga session on West 22nd Street ... Sarah Jessica Parker and Caroline Kennedy making a promotional appearance at the Barnes & Nobles in Tribeca ... Alex Rodriguez having lunch outside at Bar Pitti ... Katie Holmes signing autographs outside the Schoenfeld Theatre ... Madonna and son David walking into the Kabbalah Center ... Sandra Bernhard leaving the center with her daughter hours later ... Kate Walsh and Barry Sonnenfeld outside the Letterman show ... Britney Spears heading inside Soho House  ... and Jay-Z standing on the sidewalk in the West Village.

♦  Whitney Port's clothing line is now available! Needless to say, it's overpriced and underdesigned. [FabSugar]
♦  A juicy bit of gossip from Vivienne Westwood's Paris show last night: Kate Winslet is in the running to play the legendary designer in a Universal Pictures biopic. [SassyBella]
♦  Polygamist bouffants are now très chic, if we're to believe W and Vogue, which have the bizarre hairstyles on Linda Evangelista and Isabeli Fontana, respectively. But what's Tim Gunn going to say? [NYO] More

• It looks like Pat O'Brien might be back off the wagon following his email rant about Lara Spencer to the staffs of both The Insider and ET. [R&M, P6]
• Aubrey O'Day and Joe Francis were spotted making out at a VMA party, and now some suspect they may be a couple. [P6]
• Thieves broke into Kate Moss' Range Rover in London, but all they took was cash and a box of chocolates. [Mirror]
• It looks like on-again/off-again couple Leonardo DiCaprio and Bar Rafaeli are now on the outs, although who knows for how long. [R&M]
• Not only is Bristol Palin a pregnant teen, but she might be a boyfriend-stealer, too. [Extra]
• Some of Celine Dion's demands on tour: A dentist, a physiotherapist, 11 bodyguards, and a dressing room stocked with Bavarian figs and French cherries. [Mirror]

Jay Parts With Vegas | Jay-Z may be the richest man in hip hop, but there's at least one investment that hasn't been a homerun for the demi-billionaire: After months of rumors, the Vegas outpost of 40/40 has officially closed, and the venue will be taken over by the Palazzo Hotel. [LAT via TBS]

• A visiting Kim Kardashian was rushed to New York-Presbyterian late last night after she cut her foot on a glass coffee table at her hotel. [TMZ]
• A cop in LA pulled his gun on Diddy during a traffic stop this weekend. [NYDN]
• Marc Jacobs says he is a "perfect being" now that he has a buff bod. He also says he has 28 tattoos now and spends hours in the bathroom shampooing his hair and putting on moisturizer. [R&M]
• Paris Hilton is now hawking a line of polyester hair extensions. [NYDN]

Spottings | Tom Cruise walking Katie Holmes to rehearsals for her Broadway show ... Donnie and Marie Osmond performing on Good Morning America ... Taylor Swift leaving and then returning to her Midtown hotel ... the Jonas Brothers getting mobbed outside the Trump International Hotel ... the stars of the Dutch version of High School Musical eating lunch at Pastis ... Royston Langdon and a mystery brunette leaving Pastis ... and Beyonce and Jay-Z walking out of the Waverly Inn.