Mississippi, 2008 by Lee Friedlander, from his America By Car series. Photograph: Lee Friedlander, courtesy Fraenkel Gallery, San Francisco  In 2005, I spent an afternoon in the Museum of Modern Art in New York wandering though a vast retrospective of Lee Friedlander's work. It was a rewarding, if sometimes disorienting, experience, not just because of the number of images (around 500), but in the range of subject matter and the avid restlessness of his visual imagination.  Friedlander has photographed everyday America in all its quiet strangeness for 50-odd years now, turning his camera on streets, cars, passing strangers, buildings, gardens, trees, highways, shop windows, signs, parking lots, canyons and cows. He has made great formal portraits of jazz musicians and busy, brilliantly composed, street photographs. He has photographed Miles Davis at his most brooding and the young, yet-to-be-famous Madonna nude in her untidy New York apartment. He has even chased – and caught – his own shadow in a series of often eerily brilliant self portraits in which his silhouette looms over pavements or passers-by and is reflected back at us in a windowpane.  Now 77, and still working, Friedlander first came to public attention when the great American curator, John Swarkowski, included his work in the groundbreaking New Documents exhibition at MoMA New York in 1967, alongside equally iconoclastic photographs by Garry Winogrand and Diane Arbus. Friedlander called his photographs "social documents", but they were also challenging and often playful investigations of what photography could be; a slap in the face of the high seriousness of the American landscape tradition.  Like Walker Evans and Robert Frank before him, Friedlander went looking for America by car but he photographed it through his windscreen, creating a set of images that look like film stills from some lost American new wave film.  At Timothy Taylor, two bodies of work, both car-related, illustrate the strange cumulative power of Friedlander's approach, as well as his singular sensibility. This is photography as a kind of constant improvisation on a theme and, though separated by more than three decades, both series bear Friedlander's unmistakable signature.  The first, and most recent, is called America By Car, and comprises a selection of the photographs he took through his windscreen or out of his car window on road trips made in the past 10 years or so. The second, called The New Cars, is a portfolio originally made for Harper's Bazaar in 1964. It's a good place to start, not just chronologically, but because it gives even more evidence of his mischievous spirit and formal iconoclasm.  Back then, the high-end glossy magazine commissioned him to photograph that year's new car models – Chryslers, Buicks, Pontiacs and Cadillacs – for their November issue. Friedlander photographed the sleek and gleaming vehicles against the most downbeat backgrounds: shabby storefronts, drab inner-city car parks, and, most provocatively, a used car lot.  Rejected by Harper's Bazaar, the photographs lay forgotten in his storage space until recently, and this is the first time they have been shown outside America. They are brilliantly subversive, not least because the cars are often half hidden by other objects in the foreground or glimpsed in reflection in a store window. In one, a car is parked behind a huge pile of tyres; in another, a hood is just visible though the window of a public phone booth. You can see Harper's Bazaar's point but, as evidence of Friedlander's precocious photographic imagination, the New Cars series is revelatory.  It is also the perfect compliment to the America By Car series, in which he uses the windscreen or side window as frame within a frame, and then plays with the possibilities of that simple technique. Not that there is anything that simple about Friedlander's photographs: some are visual puzzles, others are just plain puzzling but often in a witty – or wilfully skew-whiff – way. Is that car really perched on a pole? Is that a reflection of a shop mannequin or a reflection of a reflection of a shop mannequin?  For the America By Car pictures, Friedlander stuck to black and white, but used a Hasselblad Super Wide camera, which allowed him to capture a wider vista that is often bisected by the vertical frame of the windscreen or includes a huge swath of dashboard above which buildings and telegraph poles loom. The results can be disorienting but, after a while, you start seeing America though Friedlander's eyes: how much it has changed and how much it has stayed the same.  The road signs seem oddly timeless, as do the desert motels, but the words speak volumes about today's America. A huge billboard advertises Hot Babes Direct To You. A motel sign carries the warning: Don't Take Cheques. A suburban fence bears the message: We Support Our Troops.  Recognisable skylines – Manhattan, Chicago – give way to anonymous suburbs and then the big skies and flat plains of another America of wooden houses, tall trees, cows and crows. Friedlander even traps a laughing highway patrolman in the democratic frame of his car window. In another picture, the white-haired figure on the roadside next to Friedlander's tripod is the late John Swarkowski, his first, and most important, champion. The final shot in the series is a self portrait in which the famously elusive Friedlander scowls at the viewer as if taken by surprise by his own camera.  Then again, Friedlander was often surprised by what his camera captured. When asked about his approach, he once said: "I only wanted Uncle Vern standing by his new car (a Hudson) on a clear day. I got him and the car. I also got a bit of Aunt Mary's laundry, and Beau Jack, the dog, peeing on a fence, and a row of potted tuberous begonias on the porch and 78 trees and a million pebbles in the driveway and more. It's a generous medium, photography." Or, perhaps, as these wonderfully strange and evocative photographs attest, he made it so.
Lee Friedlander has spent 50 years chronicling America through its cars – his own and other people's, writes Sean O'Hagan