Being a whale isn't all about spending the most money on the biggest property in the priciest neighborhood. It's also about throwing cash around with the type of reckless abandon that would make most CEOs and hedge fund managers cringe. That's why many of the best whales are musicians, actors, and athletes—they might not be the wealthiest people on the planet, but they're definitely the wealthiest people who are also certifiably insane. Here's a list of the top whale in each of the whale-producing fields.
Madonna managed—somehow—to own a single, marginally impressive New York City apartment, in the Upper West Side's Harperley Hall, from 1985 to 2007. That's when the wheels started to come off, as she decided to expand into her neighbor's apartment to the tune of $7 million and her co-op board decided that, no, they were not very fond of that idea. A lawsuit followed. Madonna won, closed on the adjacent pad, combined apartments, and began house hunting on the Upper East Side two years later. She ended up spending $32 million on a 26-room mansion on the wrong side of Lexington Avenue, setting a neighborhood record. (The neighborhood was subsequently referred to as "one of the worst blocks in creation" and "a jumble of soulless apartment towers.") She then began the process of gut-renovating the 57-foot-wide townhouse to give it the feel of a country estate (a country estate with a gym built on top of it, that is.) The Harperley Hall combo just went on the market for $23.5 million.
Honorable Mentions: Justin Timberlake, Lenny Kravitz, Igor Krutoy
Computer Wizard: Mark Shuttleworth
When your Wikipedia page describes you as a entrepreneur, philanthropist, and space tourist, it's safe to say you're a pretty huge whale. It cost Shuttleworth $20 million to accompany the Russians into space, but it cost him over 50 percent more than that, $31.5 million, to buy the unfinished Superior Ink Penthouse in 2010 (and he already owned another unit in the building at the time.)
Honorable Mention: Sean Parker
Actor: Sarah Jessica Parker
Of course, it's difficult to top Sarah Jessica Parker when it comes to shelling out big bucks for real estate all over the city. Although they look at far more places than they actual buy, SJP and husband Matthew Broderick have purchased, just since 2011, a West Village townhouse for $19 million, and a Brooklyn Heights townhouse for $4 million. That's in addition to the apartment Parker owns on West 12th Street, her other "work apartment" somewhere in Manhattan, and at least three houses in the Hamptons.
Honorable Mention: Jennifer Aniston
After being traded to the Yankees in 2004, Rodriguez tided himself over with an $8 million 3BR in the Trump Park Avenue (standard), and then immediately set out looking for a really impressive place. In 2008, he scooped up two apartments in, uh, Hoboken, but later that year it was rumored that he had offered "an incredible amount" of money for a 15 CPW four-bedroom. That didn't pan out and he ended up renting a 2BR in the building for $30,000/month instead (the apartment he was going to buy was later listed for $55 million.) He later spent $5.5 million on a 35th floor apartment in the Rushmore, lived there for a year, and flipped it for $7 million.
Honorable Mention: Derek Jeter
Fashion Mogul: Tommy Hilfiger
It takes a certain type of person to actually live in The Plaza, and Tommy Hilfiger is one of those people. Hilfiger briefly thought better of his 6,000-square-foot duplex in the iconic hotel, and listed it for $50 million in 2008. But, unable to find a buyer and unwilling to chop the price, he just had the place finished instead. In 2011, he was rumored to have bought the former MetLife Clocktower on Madison Avenue with the intention of turning it into a hotel, but that deal fell through. Sure he hasn't actually bought a place in a while, but when everybody just assumes that you're going to purchase a One57 condo (and he still might), you've got to be a pretty huge whale.
Honorable Mentions: Silas Chou and Lawrence Stroll
· Whale Week 2013 coverage [Curbed]