Former hip hop mogul Damon Dash ran into some money trouble a few years back (we can think of a few reasons why) and reportedly stopped paying a $78,504.20-per-month mortgage. Now comes the foreclosure auction.

Damon Dash pushing a stroller in Tribeca with a friend ... Naomi Watts carrying her son on her shoulders in Soho ... Jimmy Kimmel leaving the Trump International on Central Park West ... Hugh Jackman picking up after his dog in the West Village ... Ryan Gosling shooting scenes for his new movie in Brooklyn ... Pete Wentz pushing son Bronx around Midtown in a stroller ... Jamie Kennedy and Jennifer Love Hewitt taking pictures of themselves while walking in Soho ... Conan O'Brien chasing a taxi down Park Avenue for an NBC skit ... Michelle Williams carrying daughter Matilda in Brooklyn ... and Rihanna bowling at Lucky Strike.

Filmmaker Wes Anderson turns 40 today. Country singer Tim McGraw is turning 42. Jewelry designer Elsa Peretti is 69. Former Random House CEO Peter Olson is 59. Folk signer Judy Collins is 70. Director John Woo is 63. People's Court judge Marilyn Milian is 48. And Kelly Bensimon is 41. Weekend birthdays below.

• Rachel Roy has a new line—and it's one even her soon-to-be ex-husband should be able to afford: Roy is introducing a lower-priced collection for Macy's that she's named Rachel-Rachel Roy. [Shophound]
• Besties Shoshanna Lonstein Gruss and Charlotte Ronson are teaming up on a line called Shoshanna Made With Love Charlotte Ronson. [WWD]
• What does Karl Lagerfeld look like the morning? He'll fill you in: "I look like a madman, like something out of a horror movie!" [Fashionologie]
• "Bread-line chic" is all the rage these days. [NYT]

Good news for those of you who have little concern for the current economic or environmental climate: Damon Dash is releasing a blingy Range Rover Sport through his Tiret jewelry company which comes with "real diamond accents," 22-inch LSE alloy wheels, and a panoramic sunroof. No word on what inspired the collaboration, although given Damon's own Chevy Tahoe was recently seized by his bank after he failed to keep up with his car payments, we can only hope the deal involved him getting a new ride. [JustLuxe via Luxist]

• Things aren't looking up for Damon Dash. He's lost a fortune recently and is buried under a mountain of debt. Now it looks like he's losing his wife, too: Rachel Roy just slapped the hip hop mogul with divorce papers. [NYDN]
• David Letterman and his longtime girlfriend Regina Lasko got married last week. [NYP, Us]
• Courtenay Semel, daughter of media mogul Terry Semel and occasional girlfriend of Casey Johnson, has checked into rehab. [P6]
• The real reason behind Jen Aniston and John Mayer's split? Jen was supposedly sick of his "obsession" with Twitter. Naturally. [Sun, Telegraph]

• It may be the end of the line for socialite Tinsley Mortimer and her husband Topper. The couple has been living apart since December, reportedly because Tinz is sick of Topper's "promiscuous ways." But considering this is the second time they've been married to one another, there's always the chance the third time will be the charm. [P6]
• Gwyneth Paltrow is turning into quite the entrepreneur. She's reportedly in talks to launch a chain of gyms with her personal trainer. [DS]
• Amy Winehouse says she's finally off drugs and "feels like a new woman," although she also says that she hasn't quit drinking just yet. [NYDN]
• Madonna is reportedly beefing up her security detail following death threats from Islamic fanatics. [People.co.uk]
• A rundown of the winners at last night's Golden Globes. [E!]

• Start your engines, ladies: Sean Avery and Kelly Klein have split up. [P6]
• Mariah Carey may have collected as much as $1 million to perform three or four songs on St. Barts on New Year's Eve. [R&M]
• Lots of unresolved questions remain concerning the death of John Travolta's 16-year-old son, Jett, last week. [TMZ, NYP, Mirror]
• Get ready to see more of Lourdes Leon: Madonna's 14-year-old daughter has reportedly enrolled in Manhattan's Professional Children's School with hopes of starting an acting career. [Daily Mail]
• The new year isn't shaping up to be much fun for Gwyneth Paltrow. Her new diet bans dairy, gluten, meat, shellfish, nuts, potatoes, condiments, sugar, alcohol, and caffeine. [Telegraph]

• People won the bidding war for photos of Bristol Palin's baby, Tripp, and could be paying as much as $300,000 as part of the deal. [MSNBC]
• Mia Farrow's adopted daughter Lark died on Christmas Day. [NYDN]
• Jennifer Aniston and John Mayer spent Christmas on separate coasts, which obviously means their relationship is on the rocks. [Daily Mail]
• According to the always-reliable National Enquirer, Regis Philbin is refusing to help out his son Daniel financially, even though he's a double amputee and ekes out a living selling crafts. [NE]
• Disgraced billionaire Henry Samueli is dumping his jet to raise cash. [P6]
• The economic meltdown doesn't seem to be affecting the champagne-swilling partygoers on St. Barts this season, you'll be relieved to hear. [P6]

First Damon Dash's apartment got foreclosed upon, and now Doug E. Fresh is facing the same fate. One more to a full trend! We need more rhymes about financial planning:

A crowd of nearly 400 made their annual trip to the Bronx last Friday night for the New York Botanical Garden's 10th annual Winter Wonderland Ball. The black-and-white dinner, sponsored by Chanel, featured appearances by the likes of Cristina and Chris Cuomo, Nina Garcia, Marjorie Gubelmann, Byrdie Bell, Poppy Delevingne, Minnie Mortimer Gaghan, Steve and Christine Schwarzman, Dalia Oberlander, Gillian Hearst Simonds, Alex Kramer, Alexandra Lebenthal, Molly Sims, Holly Dunlap, Erin Fetherston, Margherita Missoni, Zani Gugelmann, Coco Rocha, Gillian and Sylvester Miniter, Bronson Van Wyck, Patrick McDonald, Stephen Knoll, Jessica Joffe, Jill Kargman, Lauren Remington Platt, Coralie Charriol Paul, Joe and Nazee Moinian, Kate Schelter, James and Whitney Fairchild, Lydia Fenet, Maggie Betts, Meredith Melling Burke, and Pamela Fiori. [PMc, Style.com, NYSD, The Daily]

It looks like Wyclef Jean and Damon Dash will have lots to chat about the next time they get together. The former Fugees star's mansion in Miami Beach has gone into foreclosure and is set to be auctioned off in three weeks. (Dash's own apartment troubles were revealed in August.) Palm Beach Post gossip columnist Jose Lambiet reports that Wyclef and several partners took out a $2 million mortgage in 2004 to purchase a canal-front estate next door to Anthony Shriver, the brother of Maria Shriver Schwarzenegger. He later embarked on a massive renovation of the property, but never ended up paying off more than $177,000 in construction costs, leading to the first in a series of liens and fines and leaving the home unfinished for more than two years. (Perhaps Wyclef should have been counting his pennies and not investing in his porn collection?) Court documents now show that Wyclef and his partners owe the bank $2.4 million, and the home is scheduled to be auctioned off on December 12th. A photo of the half-finished manse after the jump!

♦ Paris Hilton has broken up with Benji Madden after nine months of dating, reportedly so she can return to the party circuit and possibly reunite with her ex, Stavros Niarchos. The second part of Paris' plan might be tougher than she thought, though, since Stavros may have his eye on Annabelle Dexter-Jones. [Star, People, P6]
♦ Anna Wintour's reps say she has no intention of leaving Vogue. And she has no plans to accept a "cultural post" in Barack Obama's White House either, just so you know. [MSNBC]
♦ Have Madonna and Guy Ritchie finally reached a divorce settlement? The couple has supposedly sealed a deal that will let Madge keep her cash and allow Rocco and David to spend half their time living with Guy in England. [ThisIsLondon]
♦ Winona Ryder's British Airways flight had to make a special landing in London yesterday after she fell ill, allegedly because she "accidentally overdosed" on Xanax. [The Sun, NYDN]

♦ Alexander Wang was the big winner at Monday night's fifth-annual CFDA/Vogue Fashion Fund awards at Skylight Studios. Wang and fellow nominees like Richard Chai, Jason Wu, Lisa Mayock and Sophie Buhai, Irene Neuwirth, Alejandro Ingelmo, Juan Carlos Obando, Albertus Swanepoel, Swaim and Christina Hutson, and John Patrick were feted by John Galliano (left, with Charlize Theron), Anna Wintour, Diane von Furstenberg, Sally Singer, Andrew Rosen, Reed Krakoff, Jeffrey Kalinsky, Julie Gilhart, Julie Macklowe, Daphne Guinness, Sasha Heinz, Tory Burch and Lyor Cohen, Andre Leon Talley, Narciso Rodriguez, Maria Sharapova, Penn Badgley, Zac Posen, Vera Wang, Chanel Iman, Juliette Lewis, Harvey Weinstein and Georgina Chapman, Tommy Hilfiger and Dee Ocleppo, Lauren Santo Domingo, Peter Som, Piper Perabo, Phillip Lim, Lazaro Hernandez, Maggie Betts, Calvin Klein, Damon Dash and Rachel Roy, and James Franco. [PMc, NYO, Style.com, The Daily]

♦ 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]

♦ Things are going from bad to worse for Damon Dash and Rachel Roy: Three months after a bank foreclosed on their two Tribeca condos, Dash's Chevy Tahoe was seized this week after he failed to make the monthly lease payments. Does this mean he's already lost his Maybach? [NYDN]
♦ Lindsay Lohan and Samantha Ronson were supposedly getting engaged yesterday. Today the relationship is supposedly "heading for choppy waters," because Lindsay wants to "explore her heterosexuality." [The Sun]
♦ How is Lindsay's publicist explaining her client's description of Barack Obama earlier this week as the country's first "colored President"? She says no one knows what LiLo really said, since it was "unintelligible." [MSNBC]
♦ Katie Holmes is supposedly refusing to move back to LA after she's finished on Broadway. Why? Because she doesn't get dragged to as many Scientology events when she's in NYC. [NYDN]

• Gordon Ramsay says he's partnering with Victoria Beckham to open a restaurant in LA. Yes, a restaurant. Whether she'll actually taste any of the food served there is anybody's guess. [P6]

• Britney Spears is supposedly furious with her mother over her upcoming tell-all, which accuses the pop star's former manager of grinding up pills and sneaking them into her meals. She should be in a better mood, however, after she reads all the positive reviews from her appearance on the VMAs last night, where she kicked off the show and later won three awards. [P6, NYP]

Times are hard for celebrities: Rocafella Records co-founder and former Jay-Z sidekick Damon Dash (pictured, with Maybach) can't pay his mortgage! His bank has started foreclosure proceedings on his two apartments after the mini-mogul failed to pay his combined $78,500-per-month mortgage. Times are also hard for celebrity coverage: as you can see, it's been reduced to finding ways to tie in the mortgage crisis with celebrity lifestyles. The media's already expanded the definition of "celebrity" to include politicians and athletes, so playing off real estate trends is a logical next step. There's a massive news hole to fill. First Ed McMahon was foreclosed on, now this! When will it stop? We can't wait to find out! [Newsday. Pic via NYM]

Damon Dash and Rachel Roy may be darlings on the hip hop and fashion scenes, but keeping up appearances doesn't come cheap. And it looks like the couple overextended themselves a wee bit in 2006 when they took out a $7.3 million mortgage to cover two Tribeca properties—a two-floor loft in the Atalanta building at 25 North Moore Street and a spread in the Sugar Warehouse at 79 Laight Street. They reportedly stopped paying their $78,504-a-month mortgage payments in January. Now Eastern Savings Bank has filed suit against the couple to recoup the money (along with $10,000 in late fees), which means they could be facing a possible foreclosure if they can't come up with the cash. After the jump, you can look over the mortgage that got Dash and Roy into this mess.