Portraits of Vice Presidents with Octopuses on Their Heads — the Ones You’ve Always Wanted To See


Last year, after part­ing ways with a pun­ish­ing, thank­less cor­po­rate job but before my wife gave birth to my first child, my friend invit­ed me to par­tic­i­pate in the From Dusk til Drawn fundrais­er at the Muse­um of Con­tem­po­rary Art in San­ta Bar­bara. Basi­cal­ly, it involved draw­ing for 24 straight hours. At that point in my life – i.e. before chil­dren – sleep depri­va­tion was a nov­el­ty. It sound­ed insane. I was in.

I knew I need­ed a sys­tem. The last thing I want­ed was to be strug­gling for ideas of some­thing to draw at four in the morn­ing. So after some debate, I decid­ed to draw por­traits of all 47 vice pres­i­dents of the Unit­ed States. With octo­pus­es on their heads. Why?


It prob­a­bly start­ed with Wal­ter Mon­dale. I was on the couch with my moth­er watch­ing the returns for the 1984 elec­tion. When it became clear that he was not going to become America’s next chief exec­u­tive, my moth­er, who spent her for­ma­tive years in Berke­ley dur­ing the thick of the ‘60s, stood up, pro­claimed “Well, shit!” and stormed upstairs. I was in sev­enth grade. This was the first elec­tion I cared about. Mon­dale had reached for glo­ry and failed spec­tac­u­lar­ly. Start­ing that night, I became fas­ci­nat­ed with those who aspired to his­to­ry but end­ed up a foot­note. So obvi­ous­ly, I became inter­est­ed in vice pres­i­dents.

The Con­sti­tu­tion is sur­pris­ing­ly vague on the veep. Vice Pres­i­dent Charles Dawes — a man who won a Nobel Peace Prize and who wrote a tune that would lat­er become a pop hit, all before becom­ing Calvin Coolidge’s num­ber two guy — summed up the job while talk­ing with sen­a­tor and future VP Alben W. Barkley like this: “I can do only two things here. One of them is to sit up here on this ros­trum [in the Sen­ate] and lis­ten to you birds talk with­out the abil­i­ty to reply. The oth­er is to look at the news­pa­pers every morn­ing to see how the Pres­i­den­t’s health is.”

Though the posi­tion bestows on it all of the author­i­ty and pomp of the U.S. Gov­ern­ment, vice pres­i­dents through­out his­to­ry have strug­gled to find pur­pose in a poor­ly defined role, all the while wait­ing for death. It’s a bit like life itself. A few, through ambi­tion, tal­ent and a lot of luck, ascend­ed to the top job. Most moldered in obscu­ri­ty. No won­der then that John Nance Gar­ner, one of FDR’s three VPs, called the job “not worth a buck­et of warm piss.” I added the octo­pus­es because I thought they were fun­ny. It takes a rare per­son to pull off an air of dig­ni­ty with a cephalo­pod on his head. It seems to fit with the absur­di­ty of the job.


Dur­ing From Dusk til Drawn, I was a machine. I cranked out 22 por­traits of vice pres­i­dents in 24 hours. That’s one an hour, exclud­ing a 2am jaunt to get a rice bowl and a hand­ful of bath­room breaks. Over the next year, I drew and redrew them all from John Adams to Joe Biden and then, start­ing this past July, I began post­ing one pic­ture a day on my site Veep­to­pus. I’m up to Hubert H. Humphrey now. Dur­ing this time, I learned a lot about for­mer­ly impor­tant peo­ple who are now almost entire­ly unknown.  Peo­ple like William R. King, who died of tuber­cu­lo­sis three weeks after get­ting sworn in as VP, or John Breck­in­ridge, who fled to Cuba to avoid get­ting arrest­ed for trea­son. You can see the fruits of my crazy scheme here. I hope you enjoy.

Above, in descend­ing order, you can find por­traits of 1) Gar­ret Hobart (1897–1899), the 24th Veep under William McKin­ley; 2) Thomas Jef­fer­son, who bucked the VP trend and made some­thing of him­self; and 3) George Clin­ton who served under Jef­fer­son and Madi­son. Don’t con­fuse him with the guy from Par­lia­ment Funkadel­ic.

Relat­ed Con­tent: 

Watch a Wit­ty, Grit­ty, Hard­boiled Retelling of the Famous Aaron Burr-Alexan­der Hamil­ton Duel

Jonathan Crow is a Los Ange­les-based writer and film­mak­er whose work has appeared in Yahoo!, The Hol­ly­wood Reporter, and oth­er pub­li­ca­tions. You can fol­low him at @jonccrow.  And you can check out his online Veep­to­pus store here.

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