Pride Parade
The Pride Parade: the only time of the year when a 60-year-old man with a beef-jerky tan can wear a yellow banana thong and not draw attention to himself. Unlike most cities, Chicago’s Pride Parade falls on a Sunday, which gives the big event a bittersweet feeling for the working stiffs who, 24 hours later, will be fighting a hangover in their cubicles. But in a relatively short amount of time, the craziest shit goes down, and this year didn’t skimp on the standard Pride spectacles: male-to-female transsexuals wearing black tape over their Real Housewives Of New Jersey-style “buhbies,” an unlimited amount of male dancers in Speedos (is there a hotline where they order these guys?), drag queens who looked like Megan Fox, Bible thumpers, lesbians who looked like hot dudes, and the piles of garbage lining the streets afterward.
The only thing that did stand out in all of this pandemonium were the politicians, who either showed up in person or by proxy. While some of these straight-laced people looked out of place between floats of gyrating muscles and Lady Gaga remixes, others did their research and blended right in. Cook County Sheriff Tom Dart’s float was so dead-on that it put the other public officials to shame. Dart incorporated male dancers wearing sleeveless orange prison jumpsuits, which prompted someone nearby to ask, “Do you think those are real prison uniforms, and if so, are those real inmates?”

Pride regular Illinois Attorney General Lisa Madigan came out with an enormous float, which was an apt representation for someone looking to play a bigger role in Illinois politics. She's believed to be gunning for either the governor’s office or Barack Obama’s old Senate seat, and her potential competition also seized the opportunity to mingle with the LGBT community. Senator Roland Burris sat atop the back of a convertible as if he were some astronaut who just returned from the moon. But was that a campaign donation in the senator’s pants, or was he just happy to see everyone? (Note to politicians: Don’t wear khaki pants if you plan on sitting down.)

While Burris appeared mildly uncomfortable, his uneasiness was nothing compared to WGN's Bozo the Clown. Maybe he looked that way because of the weather and his makeup, or maybe he discovered some people really like clowns.

Despite heading into an election year, Cook County Board President Todd Stroger opted to sit out this parade, instead sending a rag-tag posse holding up a banner with his mug on it. Stroger showed up last year, but his move to increase the county’s sales tax didn’t get much love from the crowd, who ended up booing him when his float passed.
The stinkers included Cook County Circuit Court Clerk Dorothy Brown, who put as much effort into bedazzling her grey county van (fueled by your tax dollars) as she did in her unsuccessful bid in the mayoral race of 2007. “That’s not gay,” one person nearby calmly observed.

The Log Cabin Republicans knew how to reach out to their audience with signs like these. "Considering how many Democratics get arrested in this city, I'd almost join them," one person said.

Speaking of which, the parade lost 50 points for not including a float for all the corrupt politicians who couldn’t make it out, like former governors George Ryan and Rod Blagojevich. It would have easily knocked down Dart's Tom Of Finland reign. Go-go dancers dressed up as Ryan and Blago could dance in cages, while another dressed as U.S. Attorney Patrick Fitzgerald shoots out rainbow-colored indictments into the crowd. The only problem, however, is the float may be too big to fit on the street, because there's no telling who'll be caught next.
