Marion Barry‘s life was marked by both triumphs in public service and personal failings that sometimes undermined his leadership. He will be remembered by many in this city as a gifted, passionate civil rights organizer who dedicated his life to the betterment of D.C.’s underserved communities—-but to much of the rest of the country, Barry’s legacy begins and ends with his drug use and conviction in a 1990 FBI sting. For nearly a quarter-century, Barry has been an easy target for late-night television jokes and corrupt-politician spoofs, some of them terribly dull-witted.

In August of 1990, David Letterman gave Barry his “Top 10” treatment, with a list of potential Barry campaign slogans:

10. I’m addicted—-to public service.
9. America’s Funniest Home Video.
8. Just Say Yes.
7. I’m a Kennedy.
6. He’s ready to personally confiscate drugs.
5. Let’s put a little Colombia into the District of Columbia.
4. Hey—-here’s your Justice Department, pal!
3. He’ll get the hookers off the streets—-and into the hotel rooms.
2. Imagine the victory party!
1. I’m Barry, Barry sorry.

Soon after Barry’s arrest for crack possession, In Living Color ran a sketch starring Keenen Ivory Wayans as Arsenio Hall, who interviews Barry, played by David Alan Grier, about his recent film role (in an FBI tape) and upcoming public appearances (on trial): “You’re in the press a lot lately. You have beautiful women inviting you to hotels. People follow you everywhere you go. What’s it like to be a sex symbol?”

https://www.youtube.com/watch?v=M8vNfLtnHTc

Barry got mocked on an episode of Saturday Night Live, hosted by then-New York Mayor Rudy Giuliani, in 1997. In one sketch, Jim Breuer as Joe Pesci and Tracy Morgan as Barry try to sell drugs to Giuliani, who played himself. When he saw the clip, Barry was enraged. “I think the part about me and Giuliani was just despicable—-the implication had to do with drugs; the person playing me was rubbing his nose,” he told the New York Times, alleging that the skit played on negative racial stereotypes. ”As a fellow mayor, [Giuliani] participated in extreme character assassination. I’ve been clean over seven and a half years, and I’ve been an inspiration to a lot of the recovering community…When they gave Giuliani those lines, he should have just refused to say them.”

Most shots at Barry were throwaway jokes and easy jabs that made little thoughtful argument. Take The Simpsons: in one 1996 episode, a hired assassin who lives in an extravagant Latin American mansion picks up his phone and hears the speaker identify himself as “M.B.” “Ah, Marion Barry!” the assassin says, misreading the code. “Is it time for another shipment already?” Or the Tonight Show—-here’s Jay Leno, on a 2009 snowstorm: “There was so much white powder in D.C., people thought Marion Barry was mayor again.”

But some comedians have used Barry’s troubles with drugs and the law to critique greater social ills. On a 1996 HBO special filmed in D.C., Chris Rock shamed Barry’s presence at the Louis Farrakhan–organized Million Man March for black empowerment. “Even in our finest hour,” Rock mused, “we had a crackhead onstage,” dismayed by the fact that Barry smoked crack and got his job back, while workers in less-skilled professions would have likely been fired for good.

And on The Daily Show in May 2009, John Stewart mocked Barry’s moral high ground as the one holdout on the D.C. Council against gay marriage, a reversal of his earlier position. “Politicians ought to be moral, or we are not the moral leaders,” said Barry at the time. “I am a politician who’s moral, and you are moral leaders who are standing on the moral compass of God.” Stewart stung back: “Normally when somebody says something that oblivious to their own reality, you might say to them, ‘What are you, on crack?!'”

Photo by Darrow Montgomery