• One week after announcing he'd been diagnosed with a brain tumor, right-wing columnist Bob Novak has announced his immediate retirement. [Chicago Sun-Times]

Lenny Kravitz lookalikes in Times Square [Buenos Aires-Brooklyn]

This week's issue of Newsweek features a profile of Steve Rattner, the financier who may have earned plenty of success in the world of high finance (No. 2 at Lazard, founder of the Quadrangle Group, money manager for Mike Bloomberg), but has thus far been unable to land his dream job: running a top Wall Street bank or a Washington cabinet position. (He's 0 for 3, having backed Gore, Kerry and Hillary Clinton.) Even Henry Kravis takes a subtle dig at the journalist-turned-banker: "Ask the average guy if he knows or has heard of Bob [Rubin], chances are he has. But not Rattner." Oh, cheer up, Steve! You're still the only former Times reporter in history who ever got to stamp his initials on a $20 million jet.

We're collecting a little bit of information about Cityfile readers. That's you! It's quick and painless, we swear. And it should take three minutes, tops. Oh, and if you take part (and include your email address at the end), you'll be entered to win a $100 Bloomingdale's gift card. Thanks!

You may have heard about Zach Chodorow's new Hamptons food venture last week. The son of Jeffrey Chodorow, the mega-restaurateur behind China Grill, Kobe Club, and Asia de Cuba (among others), the 22-year-old Wharton grad is now following in his father's footsteps and selling $20 Kobe beef hot dogs outside the Lily Pond club in East Hampton. But there are two Chodorow sons living it up on the East End this summer. There's also Max (he's standing over his brother, left), who will be a sophomore at Boston University this fall. And it turns out he's following in his dad's footsteps, too: He has a criminal record!

• Kate Moss has introduced her daughter Lila to the exclusive perks of the fashion A-list: Hanging out with a bronzed, sweaty Marc Jacobs and his gay posse on a yacht in the Balearics. [Pop Sugar]

• Jamie-Lynn Sigler of Sopranos fame has sold her two-bedroom loft at 25 Leonard Street for $2.9 million. [Cityfile]

Remember the Segway, that overhyped scooter that got a ton of press a few years ago and was heralded as the device that would change urban transportation forever? Well, there's a new weird-looking scooter on the scene, the Toyota-produced Winglet, which was unveiled in Japan on Friday. It's smaller than a Segway and comes in a bunch of pretty colors. On the downside, it only goes 3.7 MPH, which means it won't be very effective for running over tourists in Midtown. A video demonstration of this little wonder after the jump.

"During the Oprah stuff I called [Bret Easton Ellis] and said, 'Dude, what the f*** do I do?" Sometimes, a quote contains an overabundance of clues to who the speaker is. Addressing the listener as dude? Cursing? Namedropping a literary hero? Invoking Oprah? Who the fuck else could it be, dude? [Times UK]

She may not be the sharpest knife in the drawer, but Gwyneth Paltrow has taken one very effective PR trick to heart: A good way to stay in the public eye when you're not actually working that much—while also appearing to care about anything other than yourself—is to lend a little time to "causes." There was her recent UNICEF PSA for preventing childhood HIV, her Key For a Cure ambassadorship, and now she's the famous face in this video exhorting American ex-pats to vote for Obama: "I'll be voting from London," she shares, "but you can vote from anywhere. If you live abroad, you've got to do it." Clearly no American in a far-off land will fail to submit to such persuasion, especially as Gwynnie uses the most familiar of her three emote-modes: earnest!

Answering machine at the (multilingual) New Jersey home of Jim Cramer, his wife Karen, and their two daughters.

Kelly Killoren Bensimon is a former model, former Gotham and Elle editor, and the former wife of photographer Gilles Bensimon. She's also the new member of the cast of Bravo's Real Housewives of New York City. So you'd think she would have thought long and hard about whether participating would be good for her career and image, right? Maybe conferred with some friends or a PR person or two? Or maybe just watched the show to see what she was getting into? Apparently not. Killoren says she hadn't watched a single episode of the show before signing on, but that she's "excited to show American women how you can live a dream life where you're taking care of your kids and working and socializing." And it's not about her. "I'm just a vehicle for the show to feature all of the amazing people I'm exposed to on a daily basis—artists, writers, athletes, actors." She really never has seen the show, has she?

Ira Rennert may be looking for some help around his Hamptons compound today. Degli and Maria Martinez, a husband and wife who served as live-in help at Rennert's 110,000-square-foot home, just quit their jobs after winning the largest jackpot in New York State lotto history. The winning ticket came out to $21 million as part of a lump sum payment, which is roughly what Rennert spends a year on gas for his fleet of jets and Hummers. [Page Six]

Barack Obama turns 47 today! He'll celebrate with fundraising events in Michigan and Boston, although he's probably much more excited about the prospect of planning a party in the West Wing next year. Also celebrating: Robert A.F. Thurman, Columbia professor, former Buddhist monk, and father of Uma, is turning 67. New York's top judge, Judith Kaye, is 70. Scandal-plagued pitcher Roger Clemens is 46. Denim designer Scott Morrison turns 36. NASCAR driver Jeff Gordon is 37. Law & Order actor Richard Belzer turns 64. Model/actor Marcus Schenkenberg is 40. And Billy Bob Thornton is turning 53.

• Mary-Kate Olsen is the last person federal investigators want to question before they close the Heath Ledger case. But the 4-foot-11, 90-pounder is refusing to talk unless she's granted immunity from prosecution. [NYP]

• Time Warner is getting ready to sell off its AOL dial-up business and may announce a deal this week. [WSJ]

• Meet the heavyweight political donors who live at River House.

Katie Holmes heading to rehearsals for her new Broadway show ... Sheryl Crow performing onstage at Rockefeller Plaza ... Rihanna getting a mani-pedi at a salon in the Village ... Disney star Selena Gomez walking with her handlers through Midtown ... Diane Kruger leaving lunch at Bar Pitti on her bike ... Agyness Deyn and Albert Hammond Jr. kissing on the sidewalk ... and Jay-Z and Beyonce heading into the Spotted Pig.

1) Lisa Salzer had a party last night for her jewelry line Lulu Frost, where hosts Alexis Bryan Morgan and Elettra Rossellini Wiedemann were joined by Erin Fetherston and Hedi Ferjani, Derek Blasberg, Luigi Tadini, Kathryn Neale Shaffer, Peter Davis, Kate Schelter, and Carole Radziwill, who were rewarded for walking up the five flights of stairs with a live Cuban band and cocktails. [Paper/style file]

Stanley Cheslock is the former merchant banker who spent four years building the Greenwich estate pictured above, which comes with a 26,000-square-foot house, indoor pool, movie theater, 12-car garage, and 3,700-bottle wine cellar. Pretty nice place, eh? Poor Stan spent some $21 million building it from the ground up. Except when he was done, he and his wife realized they'd overextended themselves a wee bit and decided to put the property up for sale. Unfortunately, the Cheslocks didn't find anyone interested in writing a check for $31 million. So he and his wife did the unthinkable: They put the property up for auction. (Like a rundown apartment in foreclosure! The shame!) The sealed bidding process started at $19 million—or $2 million less than what Cheslock paid to build it—and it ends precisely two weeks from today. More photos follow below.