Angelina Jolie is cruising the skies again. After settling into s rented estate near Calgary with Brad Pitt, Maddox and Zahara, Angelina had her instructor fly from the U.K. to Canada to continue private lessons on her $434,000 Cirrus SR22 airplane, which is equipped with a whole-plane parachute that can be activated if she loses control of the aircraft. Already a licensed private pilot, she's now tackling the tough task of learning to fly using only instruments. "She is a completely competent, confident flyer," says a source, noting that Jolie has bonded with other female flyers-to-be at the local hangar. "She just beams in the cockpit." Her tail number may help: It contains the letters "MX" in honor of her son.
JAY-Z EXPANDS HIS EMPIRE
Atlantic City's about to get a whole lot hipper, On Oct. 25, Jay-Z unveils a shoreside version of 40/40, his N.Y.C. hip-hop sports bar. Five hundred guests, including Beyoncé, Diddy, Mariah Carey, Nelly, Usher and Michael Jordan will get 18-karat platinum key invites, each adorned with a small diamond, designed by Jacob the Jeweler. (Total cost for all the invites, including shipping and insurance? $750,000.) VIPs will fly in on Caesars Palace's G4 jets for the opening, a night of free-flowing top-shelf liquor, Caribbean showgirls, Rocawear gear and hand-rolled cigars. At midnight, they'll spin a roulette wheel, and one key holder will drive home a new black Mercedes-Benz SL.
KATIE'S NEW BEAU
Katie Couric's latest love interest? Landscape painter Stephen Hannock, whom she met through a mutual pal in February. "We're cautiously dating," says Hannock, 54, who, like Couric, 48, is widowed. "We lost my wife last October. [Katie] and her cool girls have been a really big help to me and my daughter in this bumpy year. Our daughters get along great. So do we." Hannock's work, which has been shown at N.Y.C.'s Metropolitan Museum of Art, can be seen online at www.stephenhannock.com. The Today Show's rep had no comment.
BUNGALOW 8, N.Y.C. Oct. 3
Mary-Kate Olsen locks lips with a tall, young mystery man in a straw hat...
CODA, N.Y.C. Oct. 6
Cyndi Lauper does a private lunchtime gig to preview her new album The Body Acoustic, singing and playing a mean dulcimer...
ESQUIRE HOUSE, N.Y.C. Oct. 7
At an Oxfam America benefit, Jill Hennessy praises activist Bono: "He's kind of my religion. I started off playing guitar in the subways and learned using a U2 song-book." Meanwhile, Heath Ledger was overheard saying that girlfriend Michelle Williams is so pregnant she could give birth "right now," Good thing the nursery's already set up.