One hundred and eight: "Pretty Fly for a Rabbi" from Running with Scissors


One of the many miracles of Al’s careers, and when you write about Al in the depth that I have, you notice and recognize miracles, is that he’s an extremely white man who has managed to do a fair amount of ethnic material through the years yet has remained beloved. He’s slipped inside the personas, costumes and sonic outfits of pop icons of various races, genders, body sizes and ethnicities yet always hung onto his fundamental Alness, and with it the public’s love but also its understanding. 

Al’s public knows these songs are done with affection, love, care and attention to detail and consequently are quick to laugh and slow to take offense. That said, the ethnic stuff has not aged as well as the rest. I doubt that Al would include “Taco Grande” or “Lasagna” among his personal favorites, even if they’re actually less #problematic than you might imagine.

“Taco Grande” is just as adorably goofy and sadistically infectious today as it was when it was released twenty-seven year ago. Twenty seven years ago! That makes me feel old, as does my advanced age and the looming specter of death that haunts my every step. Speaking of Mexican food, The Offspring lead singer and songwriter Dexter Holland, whose “Pretty Fly for a White Guy” inspired “Pretty Fly for a Rabbi”, wrote the song to make fun of clueless cultural appropriation and both 

  1. Rocked dreadlocks for a very long time despite being the whitest man in existence, narrowly beating out best-selling author Nicholas Sparks 
  2. Owns his own hot sauce brand, Gringo Bandito, whose label features Holland in a sombrero

so maybe this wasn’t the best glass house for Holland to hurl his satirical rocks from. To paraphrase the chorus of “Pretty Fly for a Rabbi”, Oy vey, Oy vey! As people who lived through the time can wearily attest, “Fly for a White Guy” was ubiquitous and inescapable for the worst reasons. It's a glib, annoying ear worm taking lazy comedic aim at one of the weakest and most over-explored subjects for comedy ever: clueless, delusional white boys who adopt the cultural signifiers of blackness in a desperate and inherently doomed attempt to be “down.”


“Pretty Fly for a White Guy” wasn’t just annoying: it’s also pretty much a novelty song, a comedy song, an instantly dated embarrassment with corny dad joke lyrics about The Ricki Lake Show, Vanilla Ice, Pintos and how the “brothers” in “the hood” will kick your “lily white (rear end)” if you wander into their territory, a gag that was racist and awful back when it was employed in Vacation.

So with “Pretty Fly for a Rabbi” Al wasn’t taking the piss out of some ponderous pop anthem: he was making a funny song about a song that desperately tries to be funny with the same dogged and failed persistence as its deluded caucasian subject. 

Ten albums into his career as a recording artist, Al was finally dipping into the bottomless well of humor that is the Jewish joke, specifically the Rabbi joke. Al spends the entire song gushing about the titular Man of the Lord and Man of the Book, who is known and loved in his community as a big macher due to his hard work, good deals and righteous ways. 

“Pretty Fly for a Rabbi” doubles as a makeshift encyclopedia of the most commonly employed Yiddish phrases, but it’s also a collection of Jewish stereotypes, most notably the one involving Jews being cheap and bargain-hungry. Al doubles down pretty hard on this line of humor, bragging of his subject, “He does his own accounting”, “He shops at discount stores, not just any will suffice/He has to find a bargain, ’cause he won't pay retail price” and “He never acts meshugga and he's hardly a schlemiel/But if you wanna haggle, oy, he'll make you such a deal!”

Those are a lot of jokes about Jews loving to haggle and chase bargains but they’re done with such affection and care that they cease to be offensive. This faithful recycling of hoary old stereotypes made less of an impression on me than both Al’s extensive and impressive use of Yiddish slang and his mastery of not just the themes of Jewish comedy, but the specific rhythms and inflections as well. 

And as someone who is on record as going nuts over the old jokes, the dad jokes, the street jokes, the gags that have been passed down from one generation of goofball to another, it gives me entirely too much nachas that Al fulfills the prophecies of the elders and used his Rabbi song to lovingly resurrect the old gag about the best part about being a mohel (the person who performs a bris) being that they get to keep the tip, only in this case, the mohel performs the ritual circumcision, and then the rabbi gets to keep the tip, presumably in the form of both the money parents present to the rabbi and the mohel for their services and also, the tip of the penis, or the foreskin that has just been removed. 

A lot of people think Al is Jewish. “Pretty Fly for a Rabbi” will do nothing to discourage that incorrect belief. Al speaks the language of Jewish humor quite fluently, with the ease and grace of a native speaker. It’s only too fitting that Al’s big foray into the world of Judaism is defined by a very Jewish love of the possibilities of language, Yiddish and English alike. 


As a Jew, I’m flattered and charmed by “Pretty Fly for A Rabbi” rather than insulted. It’s not just Kosher; it’s worth kvelling about! 

Support the Weird Accordion to Al, independent media, join a nice communities and get nice bonuses like access to exclusive content over at