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For 51 weeks a year, Louisville is flyover territory for most of the country’s trendsetters. But for the week preceding the Kentucky Derby, the city is one of the most fashionable destinations in the world. Cool parties abound on Derby weekend — and not just for the big hat & seersucker set.

Barnstable Brown Gala (8 p.m., May 1, Barnstable Brown House) – Hosted by Doublemint Twins from the 1970s, A-listers like Tom Brady, Jessica Simpson, and Hugh Hefner mingle with C-listers like Eli Manning, Taylor Dayne, and Hef’s seven girlfriends (as well as anyone who can afford the $800 ticket) at this most famous of Derby parties. In fact, in 2004, Anna Nicole Smith met local boy and future babydaddy Larry Birkhead here. The Barnstable Brown Gala’s answer to criticism that, now in its 20th year, the party doesn’t have the draw it used to: Paris Hilton. She’s slated to attend the gala and host the official after-party at the Sports and Social Club. While this diabetes benefit is technically sold out, tickets are available from online brokers.

Hillbilly Outfield (6 p.m., May 1, to 8 p.m., May 3, 12400 Old Shelbyville Road) – Located on the outskirts of Louisville (hence the name), the $40 ticket to this benefit for the Make-A-Wish Foundation includes “drinks, food, live music, audio and video Derby coverage, games, maybe even a dip in the pool.” Hosted by the Hillbilly Coalition and now in its ninth year, this three-day festival is geared toward “anyone and everyone who can have a respectable and fun time partying their ass off for the Kentucky Derby.” How does that atmosphere differ from the infield, 21 miles away? The word “respectable.”

The Derby Spectacular (9 p.m., May 1, Glassworks) – Hosted by Kim Kardashian (and based on the publicity photo, her push-up bra as well), this party will be spread out over four floors, including the roof that offers one of the best views of Louisville and the Ohio River. This facility “dedicated to the art of glass” is fitting for a party hosted by a woman who gained fame via an amateur sex tape. When not hosting a Derby party, Glassworks offers hands-on “Blow Your Own” events, including “private group blows.” Tickets start at $150 — which probably doesn’t include a blow.

The Unconscious Collective (May 1, artist reception 6-9 p.m., music 9 p.m., Derby City Espresso) – The opening reception for this group art show features a drum circle, concert, and spoken word performance featuring beat poet Ron Whitehead. While the party at this eclectic bar/coffee shop will expose visitors to a hipper and artsier side of Louisville than what they’re probably expecting, don’t expect too much talk about the 10th race the next day at Churchill Downs.

Goodtimers 2009 Derby Eve One Night Stand (10 p.m., May 1, The Pointe) – With a promoter that focuses on “urban entertainment” and room themes that include new school, old school, and reggae, this party’s target demographic should be obvious. Michael Jordan, Terrell Owens, and BET founder Bob Johnson attended it last year, along with about 2,220 other guests. Now in its 11th year, the bash has moved to The Pointe, a cool, reclaimed industrial warehouse in Louisville’s former meatpacking district. Tickets start at $18.

The Mother of All Derby Week Parties (7 p.m., May 1, Phoenix Hill Tavern) – Theory of a Deadman highlights what Louisville music journalist Eddie Metal claims will be a “popular show with lots of hot chicks in attendance.” (I want to like the metalheads, I really do, but Butthead imitations are so passsé.) Seven other bands are playing that night too. Phoenix Hill Tavern is hosting similar Mother of All Derby Week Parties all week. Tickets for Friday night are $20.

Derby Nights Free Concert with O.A.R. ( 8 p.m., May 1, The Sports and Social Club) – Rock band O.A.R. headlines what’s expected to be the weekend’s biggest party, held at Fourth Street Live! (exclamation point theirs; Louisville’s answer to Baltimore’s Inner Harbor doesn’t merit such punctuation). But bigger isn’t always better; while other events offer the possibility of rubbing elbows with celebrities, here you’ll be mingling amongst tomorrow’s infield crowd (unless you stick around for the celebrity party afterward, which will be hosted by Paris Hilton — but would you really want to rub anything with her?). Tickets are free, but if you crave exclusivity, $100 will get you on the Hard Rock Cafe’s VIP patio.

Grand Gala (8 p.m., May 2, Galt House East) – Saturday night’s marquee event is this black-tie affair at one of Louisville’s most historic hotels (generals Grant and Sherman planned the strategy that led to the Union capturing Atlanta in 1864 at the original Galt House). Slated to attend this year: Michael Jordan, Star Jones, and Idris Elba, who apparently found the legitimacy that Stringer Bell never did.

The Down & Derby Party (8 p.m., May 2, Water Tower) – With all of the celebrities and reality TV stars in town, you’d think the gay community wouldn’t need a party of its own. But with most of the events being held on Derby Eve, someone had to keep the party flame lit through the weekend. This gay and lesbian event is sponsored by pistachio liquor maker Dumante Verdenoc (which deserves credit for encroaching into bourbon country) and benefits HIV/AIDS charities. And because stereotypes don’t invent themselves, the Derby City Roller Girls will be there. Tickets are $20.

Mutant Bar Party (8 p.m., May 1, Cinema de Lux 20: Stonybook) – While Louisville might be best known for square aspects of Americana such as baseball bats, horse racing, and Colonel Sanders, it also gave the world iconoclasts like Muhammad Ali, Hunter S. Thompson, and a festival dedicated to The Big Lebowski. So if you’re looking for a break in Derby-related activities and want to help keep Louisville weird, check out the Mutant Bar Party, where “It’s time to whip out your spandex and leather to defend a world that hates and fears you.” Tickets to this Wolverine-themed event are $16.
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