One's initial reaction to the inclusion of comedian-of-the-moment David Cross in the New York Press's recent list of the "50 Most Loathsome New Yorkers" might be one of shock: why would the Press include the droll, caustic, politically-active heir to Lenny Bruce in their list of genuine "frauds, blowhards and bloodsuckers" like Sophia Coppola, The Hilton Sisters, Chuck Klosterman, or the guy that coined the term "metrosexual"? One could excuse it as a crass marketing ploy: the Press changed hands last January, and editor Jeff Koyen and his young crew (which includes Matt Taibbi, co-founder of Moscow's notorious expat rag the eXile, who no doubt conceived of the "Most Loathsome" idea) have something to prove -- what better way to call attention to yourself than by skewering some of NYC's most sacred cows?

Yet the Cross entry is also lazy and disingenuous: sure he's "meandering" and "undisciplined" -- but "not funny"? Anyone who's seen him pantomime the crucifixion ("shit, you're out of nails? How 'bout I cross my feet like this?") or heard his dead-on impressions of Ricky Henderson, fist-fighting rednecks, and gay men ordering pizza on his Grammy-nominated Shut Up You Fucking Baby knows this is a lie: Cross is hilarious. Yet while the anonymous author calls for Cross's beat-down at the hands of a brass knuckle-bearing Andrew Dice Clay, the introduction to the list reveals that the Press's hearts are in the right place: the "Loathsome" list is not so much the product of hatred, but one of "highly enriched concern."

And any good David Cross fan should be concerned when the Press gloats over Cross being cursed off of stage in Little Rock, as captured in his recent Let America Laugh tour DVD, for being "smug" and "condescending" -- because it's true.

But why?

We might consider it a symptom of a much deeper problem: Cross's inherent self-contradictions. A near-militant left-wing radical on the one hand, and a weird fixture of prime-time TV and blockbuster movies on the other, Cross seems caught between the worldly excess of your typical entertainer, and the firebrand self-righteous anger of a punk rock activist. David Cross isn't loathsome, he's lost.

The DVD, whether it was intended to do so or not, drives this point home: documentarian Lance Bangs follows Cross as he tours the country in a van with twenty-something opening act UltraBabyFat to unleash five-star political torrents on the "deaf ears and loud mouths" (as the Press dubs them) of college-age "Mr. Show" fans around the country. The Little Rock incident was less a case of drunk rednecks taking offense to Cross's "acidic New York wit" and more one of overly-excited fans showing their love in undisciplined ways. And love him they do: Shut Up You Fucking Baby opens with Cross thanking his audience in advance for all the free pot, CDs, and demo tapes they will no doubt shower their hero with following the show.

By the end of documentary, after Cross has a one-night stand "just for the experience" with a twenty-something blonde bombshell who meets him backstage in San Diego, it become quite clear that Cross, who turned forty on April 4th, is slumming it.

If Cross is smug and resentful of his audiences it's because, as a comedian, he has run out of options. His hatred for the traditional comedy club circuit (where one might find comedy of the "hey, what if 'We Are the World' was sung by the cast of Friends?" variety, as Cross points out on Baby) is clear, and one can only guess that his bizarre appearances on sitcoms like "Just Shoot Me" and Republican-owned FOX TV's "Oliver Beene," and "Arrested Development", along with mainstream movies like Men in Black and Scary Movie 2, are for the money and the "experience." The punk clubs may give him the leeway to try out new, even more controversial material on an audience already familiar with it, and to party his ass off -- Cross's reputation as a drinker is legendary -- but it is clear that his biting political satire isn't winning over any new converts. Cross, simply put, is afraid to grow up.

In a recent video interview the activist site MusicForAmerica.org conducted in New York's Thompson Square, Cross is asked his opinion on the failures of last year's activist movement to stop the war in Iraq.

Yet this is the same man who, in a performance at a $250/plate fundraiser for Howard Dean last December, raised the ire of the Deanster and the NY Post for his use of the word "nigger" in a bit about Trent Lott. That the epithet was taken out of context is beside the point (Cross was only mimicking Lott's racist Mississippi drawl): like the baring of breasts and the un-shaving of armpits, Cross's deeply-held personal preference for angry, caustic comedy makes progressives look bad.

Elsewhere in the interview, Cross expresses his contempt for comedians who preach to their audiences:

And yet he does it a lot. Shut Up You Fucking Baby is remarkable for the sheer amount of firepower Cross unleashes on "that fucking asshole" George W. Bush, Donald Rumsfeld, the Christian Right, and the "willfully ignorant" and "self-centered" Americans who voted for them. When he lambastes voters "too busy to log onto The Guardian UK" to educate themselves, you can hear the audience's nervous laughter: most people -- Right or Left -- are too busy to log onto The Guardian UK.

Yet for all of Cross's dogged harassment of the Right Wing, in his quieter moments you suspect he's willing to give his straw men a chance. In another interview from early this year, this time with Wiretap Magazine's Dan Hoyle, Cross admits:

While not exactly a stage-worthy sentiment, Cross's surprising, politically-nuanced willingness to give the other side its due may hold the key to his future: running for office. Thankfully, Cross himself is aware of this future role he could take on ("My guess is it would be either something to do with the city of New York or a representative of a district in Manhattan," as he told Hoyle), and to kick-off this new chapter in the Cross career, Dave is planning a "get out the vote" comedy tour for the summer run-up to the election in November.

His "Loathsome" ranking, then, couldn't have come at a better time. Cross needs all the encouragement he can get to tone down his language, polish his criticisms, and leave behind his frustrating comedy career to become the leader he knows we need. Go get 'em Dave!