Several weeks ago, in the throes of New York apartment hunting, I called a man who had advertised a reasonably priced loft on Craigslist. He was very friendly and wished to talk about everything but the apartment itself.“What is area code 202?” he asked me, his accent thick and untraceable. “From what city are you?”“Oh, 202 is Washington, D.C.,” I told him.“Ohhhh,” he replied, stretching the word to four distinct syllables, “the city that re-elected Marion Barry!”***It’s sad, but it’s true: Marion Shepilov Barry Jr. really is an iconic Washingtonian. Presidents and senators come and go, but Barry is in the District to stay.Back in 1990, while mayor, Barry found himself in Washington’s Vista Hotel smoking crack cocaine with a female friend. As he soon learned, the room was under video surveillance, so that when the FBI and D.C. police confronted and arrested Barry, his immortal words—“Bitch set me up”—were captured, broadcast, and rebroadcast for years to come.Of course, even a conviction and a prison sentence couldn’t keep him out of office for long, and in 1994, Barry was reelected to a fourth mayoral term by the city’s overwhelmingly Democratic population. Lifelong liberals, my parents were for once divided. My mother exercised caution and voted Republican. In a fit of blind loyalty, my father stood behind Barry.I was 10 when Barry made his triumphant return to the mayor’s office, and I was more than a little confused. Washington is a place of politics and, theoretically, accountability. Men in suits arrive, and if they don’t do their jobs well, they are eventually replaced. The District is full of out-of-state plates and people born elsewhere. I never understood why Barry didn’t go away.And when I was young, Washington was also a magical place, full of gleaming white buildings and solemn memorials and mysterious black government sedans. But the press surrounding Barry’s rises and falls directed me, for the first time, to the uglier aspects of the city. Beyond the postcard images and the floods of tourists lay crime and violence so severe that many dubbed Washington the murder capital of the world. The District’s public education system was in shameful shape, and I became painfully aware that I lived in a small white enclave far removed from the city’s majority black population.Yes, I slowly learned, Washington was not always the inspiring metropolis that guidebooks and movies had promised me. And if Barry’s escapades hadn’t taught me such sad truths, surely some other scandal would have.And yet we often see that people much prefer to laugh at misfortune or embarrassment than to cry over it. The talk shows went crazy for Barry. I remember that the 1996 comedy “High School High” was set in inner-city Marion Barry High. I have a sweatshirt that asks, “Washington, D.C.: Wanna be mayor?” And the other day, I noted that an old friend’s Facebook profile lists “the bitch set me up” as her hometown. I can always get a laugh from Googling the words “Marion Barry + quotation,” which yields dozens of sites with the same ridiculous list of excerpts. Many admit to skepticism about the material’s authenticity, but the excerpts are amusing nonetheless. For example: “People have criticized me because my security detail is larger than the president’s. But you must ask yourself: are there more people who want to kill me than who want to kill the president? I can assure you there are.” Another gem: “First, it was not a strip bar, it was an erotic club. And second, what can I say? I’m a night owl.”Often enough, however, I feel guilty for laughing. What does it say about my beloved city that Marion Barry has become an icon of sorts, with all of these sites devoted to the ridiculous things he might have said? Washington’s struggles are mirrored by Barry’s, and his example should be more cautionary than funny.Though no longer mayor, Barry is still riding high in D.C. Despite repeated drug and legal troubles in recent years, he has a seat on the city council. Back in the early ’90s, when he was first released from prison, Barry ran for a council seat before returning to the mayor’s office. According to Wikipedia, his first post-incarceration campaign slogan was “He may not be perfect, but he’s perfect for D.C.” Wikipedia is unreliable, of course, so you can take those words or leave them. But even if they and the list of outlandish quotations aren’t all true—even if somebody made them up—they were composed with a very specific comical image in mind.I love Washington, and I love to laugh, but I have come to realize that laughing at Washington and its embarrassments is a means of deflecting self-criticism and discomfort. Pride in one’s hometown need not be pride in its screw-ups.