The album belongs to a more innocent, pre-Edgelord era in pop-culture trolling, when being actively offensive was considered a noble action against a rising establishment whose Democratic and Republican voters found common cause in blacklisting. It was the era of Howard Stern's peak, Bill Hicks' rise to alt-comedy sainthood, and Dennis Leary playing the Stone Temple Pilots to Hicks' Nirvana in his MTV commercials. Heck, even a young Radiohead was naming albums after Jerky Boys sketches. As a suburban couple far more interested in food than politics, Ween didn't project the same kind of outwardly hostile energy as the aforementioned contrarian cranks. But their deceptively nice demeanor meant they could get away with pushing the envelope even further.
While Freeman and Melchiondo would cringe at the label “comedy rock,” they approached the music like a sketch troupe: Each song was its own self-contained absurdist environment, each presenting a new opportunity to reinvent themselves with different sounds, scripted and some possibly ill-intentioned, but performed with fake cast accents (see: the spoof Mexican murder ballad “Buenas Tardes Amigos” or the Middle Eastern mutant metal of “I Can't Put My Finger On It”, possibly the first and song ever inspired by the stench of falafel).
And like great comic actors, Ween can convey an entire universe with simple details: On the opening honky-soul swinger “Take Me Away,” Freeman drops a Swiss “thank you” to a standing ovation, and you're immediately into a sparsely attended nightclub somewhere in the Midwest circa 1974, seeing some aging and bloated former pop icon desperately trying to stay hip 15 years after his prime. You can practically imagine the sweaty overgrown sideburns, the unbuttoned shirt and the hanging bow tie. It's no coincidence that some of Ween's most vocal fans are sketch comedy creators themselves—Mr. The Show, Tim and Eric, the South Park kids and Tenacious D. (And at a time when the alt-rock world was still mourning the death of Kurt Cobain, Ween dedicated Chocolate and cheese to the latecomer SCTV the great John Candy, who died a month before him.)
But where their previous albums risked degenerating into laughable, Chocolate and cheese he never breaks the fourth wall or winks at the camera. It effectively traps the listener in deeply uncomfortable situations where you are forced to ask yourself: Am I supposed to laugh at this? The central ballad, “Baby Bitch,” perfected Elliott Smith's acid acoustic serenade before Smith became synonymous with the form, but its wounded heart is connected to a gangsta rap mastermind. The song captures the unresolved grudges that bubble up when your ex reappears after entering a new relationship. But while countless dorm rooms across America have collectively burst into laughter at the sound of Freeman humming “fuck you, you stinkin' ass ho” over maddened guitar strums, the song is just as flattering a portrait of male insecurity and self-loathing. the Afghan Whigs were dying out at that time.
