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Remembering My Friend Pete Doolittle, Anarchic San Francisco Artist

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white man in glasses smiles while holding up window pane with painting of robot
Pete Doolittle behind a work in progress — one of his signature window paintings. (Courtesy of Pete Doolittle)

The morning after New Year’s Day, one of my oldest friends in San Francisco very suddenly, quite unexpectedly, died. His name was Pete Doolittle, and if you didn’t know him personally, you might know his distinctive paintings that were most often rendered on discarded window panes.

Pete’s loss is a significant one for an awful lot of folks in San Francisco. His friends, his family, his fans, his neighbors in the Haight. But it’s a loss for the city too. Because to me, Pete Doolittle was one of the last bastions of a San Francisco underground that has in many ways vanished — one that I am grateful to have experienced by his side.

I first met Pete in 2002, when we were both adrift and trying to find our feet in San Francisco. We were newbies in the city and I was introduced to him by a mutual friend who knew Pete from Minnesota. Pete, 25 at the time, wasn’t a professional artist yet, but he sure did doodle on bar napkins a lot. He still went by his birth name, which he hated. I’ll leave it unsaid out of respect, but it’s still the secret name I call him by in my head.

Back when we met, San Francisco was awash with folks like me and Pete: struggling creative types with quiet ambitions that mostly had to do with avoiding boring jobs and/or living conventional lives. We were chronically broke and barely feeding ourselves, but we always managed to acquire beer. We both had stints of couch surfing. I was just learning how to hustle enough to scrape by but Pete was already well-versed in the practice, and an enthusiastic teacher.

A collage of four photos, all featuring colorful, cartoonish paintings.
Pete Doolittle painted almost exclusively on discarded window panes. (Courtesy of Pete Doolittle)

Pete was the first person who ever showed me how to dumpster dive. I don’t remember much about the location now, but I do remember that he had a very specific pair of socks he wore for such occasions. They were knee-high, stripy and in no way impervious to filth, but the look of unabashed glee he got every time he pulled them on was completely infectious.

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One of Pete’s most memorable dumpster scores was a child’s Spider-Man costume. He recovered the outfit, somehow managed to squeeze into it, and took it upon himself to go down to Pier 39 to tap dance in the street for tourists. He looked so patently ridiculous, passersby didn’t know whether to laugh at him or pity him. Either way, something about this grown man in that tiny costume inspired audiences to cough up. He wound up making a stack of cash that day. We celebrated with whiskey that night.

Pete was generous with whatever he had. I still have a Haight Ashbury Youth Outreach handbook that Pete proudly hand-delivered to me that first year, for the sake of my survival. Inside are listings for free health, dental and eye care resources, places to get free food, clothing and showers, instructions on how to get social security assistance and even information about how to escape abusive relationships. It also happens to contain step-by-step instructions on how to “safely” inject narcotics (actual quote: “Not in yer neck!”) and what not to do if someone is overdosing (“Do not inject the person with speed.”)

I have held onto the book all of these years, partly because it is a perfect time capsule of San Francisco street culture in the early 2000s, and partly because it reminds me vividly of my early friendship with Pete. He somehow came by this tiny goldmine of resources and then just willingly handed it over to me.

A book cover featuring a skull and crossbones and handwritten lettering.
The ‘Haight Ashbury Youth Outreach Team Resource Guide’ from 2001 that Pete gave me, complete with notes. (Rae Alexandra)

My admiration for Pete was immediate and born from his scrappiness, confidence and unfiltered saltiness. He was the first person who ever pointed out to me that my boyfriend at the time was a monster. “Don’t trust that man,” he told me. “He’s not who you think he is.” When my relationship imploded after a three-month marriage, I was able to return to Pete and congratulate him on being entirely right. He didn’t take the opportunity to gloat. “I’m just glad you’re out of it,” he shrugged.

My abysmal taste in men did, however, provide Pete with something that would turn out to be incredibly important. One night, Pete knew I was at the boyfriend’s home on my own, so he paid me a visit. When he stepped into the living room, Pete was immediately taken aback by a piece of art hanging next to the couch. It was a depiction of an abstract figure and a few pieces of detritus, but it was painted on a framed window pane.

Pete immediately had a multitude of questions about it, none of which I knew the answers to. I have to wonder now what direction Pete’s art would have taken if he’d never seen that window painting in that terrible man’s living room. Pete’s attatchment to that particular format has been so enduring, his name is now more synonymous with windows than probably that original painter.

A man wearing a hoodie hunched over a table strewn with spray paint cans making a pen drawing of a robot.
When we first met, Pete’s GAME OVER knuckle tattoos were just about the coolest hand tatts I had ever seen in my life. (Courtesy of Pete Doolittle)

In 2013, when my second husband died — the man from Minnesota who had originally introduced us — Pete presented me with an incredible gift. I was scrambling to raise money for the funeral and Pete wanted to help. He made a painting to auction off, with all proceeds going into the funeral fund. He opted to paint a rendition of our lost loved one, titled No Umbrella. The first time I saw it, I burst into tears. In simple bold strokes, Pete had captured the essence of Jef entirely. A teddy bear wearing a smiley face, head bowed in sorrow, left out in the rain, hearts clutched in his hand.

In the end, Pete’s painting brought me the single largest donation I received for the funeral. Shortly afterwards, I got a slightly edited version of the painting tattooed on my left forearm. It’s an image I will treasure always.

A tattoo depicting a figure holding an arrow in one hand and two hearts in the other, wearing a teddy bear costume with a smily face on the torso. The figure is looking down sadly, blue streaks falling all around him.
My tattoo, as it looked the day it was finished, based on the painting ‘No Umbrella’ by Pete Doolittle. (Rae Alexandra)

A few years later, Pete was being a curmudgeon about something, I got mad and we wound up having a major spat that dragged on for two years. It only ended when we finally ran into each other at a punk rock show. As soon as we saw each other face to face again, we just hugged, picked up where we’d left off and forgot all about our stupid rift. I let him back into my life and was immediately relieved to have done so. Now, I am enormously grateful that we found a way to fix things before it was too late.

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Much of how I think about Pete has to do with survival. How he helped me to survive in those early years. How he survived as a fiercely independent artist in one of the most expensive cities on Earth. For him to be gone is still entirely unfathomable to me. I am only grateful that he will live on in the many colorful panes of glass he left hanging in every corner of the city. As long as they’re still here, part of him will be too.

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