Day One hundred and forty-four: "Skipper Dan" from Internet Leaks


During the Ridiculously Self-Indulgent Vanity Tour, we got a fascinating glimpse at what Al’s shows and career might have been like if he’d never rocketed to improbable yet enduring superstardom as the most successful parody artist in the history of American pop music, a household name revered by generation upon generation of geek as a hero and role model. 

We got to experience what a “Weird Al” Yankovic show looks and feels like without the props, costumes, bit players, screens upon screens upon screens and the stagecraft Al usually employs to reproduce the look and feel and iconography of his iconic music videos as closely as possible.

For at least one sublime tour, Al was able to cast off the shackles and expectations of pop stardom and be a musician, a cult artist, a veteran troubadour taking his stories, songs and show from town to town, to a more adult audience than he’d ever entertained before. 

There’s only one “Weird Al” Yankovic. Pretty much every facet of his career is unique, from the half parody/half original formula of his albums, to the requisite polka medley of recent hits to high-tech concert extravaganzas where Al rocks everything from fat suits to flannel to step inside the outsized personas of four decades of pop icons. 


But Al is not unique in writing and performing funny songs. On the contrary, many, if not most, of my favorite songwriters and musicians are funny. To cite a timely example, Boots Riley of the Coup is easily one of my top five all-time favorite rappers because he is  hilarious. Humor is a big part of what makes Coup albums so much fun and accessible despite the incandescent, righteous political rage at their core. 

The Ridiculously Self-Indulgent Vanity Tour gave Al an opportunity to tour like Loudon Wainwright III or Kinky Friedman, two fellow Dr. Demento Show favorites who can travel the world entertaining crowds with just an acoustic guitar, a deep, deep catalog of great, funny and sometimes heartbreaking songs and a surplus of charisma rather than having to mount an elaborate multi-media extravaganza every time he hits the stage. 

More pertinently to the song we’re discussing, The Ridiculously Self-Indulgent Vanity Tour gave Al a chance to be like Fountains of Wayne’s Adam Schlesinger, who writes funny, melancholy story songs for his band, other people and the stage and screen while remaining relatively anonymous. 

I’m a huge Fountains of Wayne fan and I honestly could not tell you what Adam Schlesinger looks like whereas I can vouch that Al can’t go to a restaurant without everyone whispering about the celebrity in their midst. 


“Skipper Dan” was designed as a Weezer pastiche and while I was into Weezer back in the day, my brain refuses to see it as anything other than a tribute to the wry story songs and infectious power pop of Fountains of Wayne. 

“Skipper Dan” is a fascinating and refreshing anomaly in that it feels less like comedy music, where the comedy aspect is as important and central as the music, and more like an infectious rock and roll song that just happens to be funny. The humor in the song is subtler and more melancholy than Al’s usual fare. Instead of being rooted in insanity of the harmless and exceedingly harmful variety or obsession, it’s rooted in an unexpectedly life-sized sense of personal and professional disappointment.

This agreeably off-brand sleeper doesn’t introduce its central comic conceit until over a minute has passed. We start off slowly, with the titular thespian radiating all the promise and potential in the world as not just any old aspiring actor but as a future giant of the stage and screen, a high school theater superstar, Juilliard graduate (like Al himself, he graduates valedictorian) and acting-class virtuoso destined for great things, for glamorous photo shoots and Tarantino movies and Broadway glory. 

Yes, the under-employed thespian kvetching to us in song is full of hope, big dreams and great expectations that die a painful, unmourned public death when the best he can manage as an actor is prostituting his talents for a humiliating but consistent payday as tour guide “Skipper Dan” on the Jungle Cruise Ride at a theme park prison known as Adventure Land. 


The gig's vague proximity to actual acting somehow just seems to make everything worse. This is an artist whose suffering soul angrily demands to recite Shakespeare in front of rapt crowds yet he’s stuck telling the same abysmal jokes over and over again, dying a little more inside with every canned wisecrack and endlessly repeated faux-ad-lib. 

The delightful digital single and highlight of both Internet Leaks and Alpocalypse finds Al eschewing the usual trash and low-culture signifiers, like Brady Bunch and fast food in favor of uncharacteristically middlebrow, and even highbrow references to actress/acting teacher/author Uta Hagen, David Mamet's Speed the Plow and celebrity photographer Annie Leibovitz.

My stupid brain refuses to buy this as anything other than a Fountains of Wayne riff because one of the things I love about the group is its genius in combining humor with deep sadness and virtuoso song craft as Al does here. To be honest, I think “Skipper Dan” is just too good to be a pastiche of a second-rate band like Weezer but it perfectly captures the literate sadness that makes Fountains of Wayne so special, albeit to a cult a fraction the size of Al’s audience, both in terms of casual fans of his parodies and the die-hards who flocked to Al’s last tour. 


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