Cityfile: New York's Most Notable and Influential

• Friends worry Jessica Simpson is "at the lowest point of her life" now that she's lost her beloved dog, Daisy. Others say she's coping "better than her friends may realize." Either way, we she's probably feeling much better now that her friends are sharing her innermost feelings with the tabloids. [People]
• The man suspected of breaking into Lindsay Lohan's house wasn't a complete stranger: The two reportedly hung out on the set of her film Labor Pains last year. The girl's not the best judge of character, as you've probably realized by now. [TMZ]
• The drugs that were prescribed to Anna Nicole Smith amounted to "pharmaceutical suicide," according to newly unsealed court documents that were obtained by the LA Times. Most disturbing: The documents also reveal that both of Anna Nicole's doctors "transgressed professional boundaries by having sexual contact with their famous patient." [LAT]
• Michelle Obama gave Barack the silent treatment at points during his campaign for president because she was pissed about all the women throwing themselves at him, according to a new book. There was even a hot young campaign aide who was mysteriously "relocated" after developing a close relationship with the President. [NYDN, P6]
• Did you catch President Obama's appearance on Letterman last night? [MTV]More

• Lindsay Lohan certainly had an eventful weekend. After a judge issued a warrant for her arrest on Friday, Lindsay had a meltdown on Twitter and ended up in a fight with Sam Ronson that was so intense, the cops had to be called. It's not over yet: She's scheduled to appear in court today, although she may not show. [People, Gawker, TMZ, NYP]
• Olivia Palermo isn't making friends in her Tribeca apartment building. She strutted past the people gathered in the lobby last Thursday "completely oblivious" to the fact that one of the building's apartments was on fire. [P6]
• Gwyneth Paltrow and her trainer Tracy Anderson are having trouble finding people to pay $4,500 to join their new Tribeca gym. What a surprise. [P6]More

• Hope you're sitting down for this one. Donald Trump Jr. and his wife Vanessa had a baby yesterday. It was a boy. And he will now bear a burden for the rest of his life: His parents named him Donald J. Trump III. [People]
• Lindsay Lohan is launching a self-tanning line called Stay Gold. Finally! [NYDN]
• "Real Housewife" Bethenny Frankel was spotted using coupons at a hair salon. [P6]
• After dating for about half a century, Harrison Ford and Calista Flockhart may finally be ready to get hitched. [Cindy Adams]
• Please note that Walter Cronkite is not related to social/art scenester Kipton Cronkite, despite his claims to the contrary. [P6]More

♦  Guy Ritchie supposedly cried after seeing son Rocco wearing a Yankees t-shirt this week. So sensitive! Or maybe not so much: Ritchie also reportedly described Madonna as "old, fat, ugly and wrinkled," and said she couldn't sing. [Us, NYDN]
♦  Not only did Lindsay Lohan's stint on Ugly Betty get cut short because she didn't get along with America Ferrera, LiLo clashed with everyone else on set, too. Also, she enjoys snipping out photos of herself from the tabloids. [P6]
♦  Jennifer Aniston's publicist is denying she's pregnant. [ET]
♦  Gossip Girl's Taylor Momsen spent four days in the hospital with a "potentially life-threatening throat-infection." But she was miraculously cured and released yesterday afternoon. [Us] 
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♦  Samantha Ronson refused to DJ an event at Rubyfruit, allegedly because she doesn't spin at gay or lesbian bars. Her rep, of course, denies this. [P6]
♦  David Spade didn't turn up at Eric Trump's charity golf tournament in New Jersey last week because he thought it was taking place at Trump's LA course. [P6]
♦  An Atlantic City monsignor wants his name added to the list of Raffaello Follieri's victims. He says he gave the Italian playboy $110,000 because Raffaello said he needed the funds to pay some nuns. [NYDN]
♦  MTV has finally confirmed Whitney Port's Hills spinoff. It will begin airing in early 2009. [E!]
♦  How exciting! Mike Bloomberg will become an honorary citizen of Tbilisi, Georgia tomorrow night. [P6]More

• Alessandra Ambrosio just gave birth, but she isn't wasting any time. She's reportedly already looking to sell pictures of her newborn daughter Anja to the tabloids. [P6]
• Real Housewives star LuAnn de Lesseps went to Todd Rome and Vanessa Brahms' Southampton wedding, where she may have gotten drunk, sang songs, and tried to make out with a married man. This may also explain why she reportedly got into a fight with her husband afterwards in the parking lot of Nello's. [P6]
• Rafael Nadal didn't care much for the photo of him on the cover of last week's New York. The tennis star says it went "further than he was comfortable with." [MSNBC]
• Guy Ritchie says he's not a follower of Kabbalah, and that he and Madonna may "possibly" be adopting another child from Malawi in the future. [OK!, Observer UK]