San Francisco Street Sighting - 1958 Oldsmobile Super 88 Holiday Coupe

I don't make it to San Francisco much anymore. I've been out of college for several years, working full time, and now with the coronavirus pandemic going on I've barely gone anywhere for the past few months. These pictures are two years old but they continue a long-held tradition. When I go to the city I always try to see if our friend Fifties Guy has anything new. This visit was after I participated in my first Radwood car show in South San Francisco, where I shined up and displayed my 1999 Buick Regal GS. I'd already paid the bridge toll to be on the peninsula, so I headed up north for a little while. Sure enough, I was greeted by this all-original 1958 Oldsmobile finished in what I believe to be Champagne Mist Poly.

Livermore Street Sighting - 1955 Oldsmobile 88 Holiday

One of the defining characteristics of 1950s car styling is ostentation. Two- and three-tone paint jobs, tail fins, whitewall tires and lots of chrome trim everywhere are what most people associate with the era. But occasionally one comes across a car that does an awful lot with very little. I have come to really like the simpler designs of cheaper models that make do with less ornamentation. Some mildly customized cars like this 1955 Oldsmobile 88 can also pull it off.

San Francisco Street Sighting - 1986 Oldsmobile Firenza Coupe

Of all the cars featured on California Streets, a Chevy Cavalier isn't most people's first idea of a rare classic. It isn't even on most people's list of classic cars. So why are you looking at one on this website? Because you aren't, it's an Oldsmobile Firenza Coupe. Same difference, you say? Yeah, it's a GM J-body compact that shares 90% of its body and parts with a Cavalier. But this one features bespoke fascias and wheels, and other goodies that you really can't get anymore. Not many people bought Firenzas when they were new and the aftermarket is nonexistent.

San Francisco Street Sighting - 1972 Oldsmobile Vista Cruiser

A lot of people are familiar with the Wagon Queen Family Truckster from National Lampoon's Vacation. Anyone remember what Clark Griswold traded in at Lou Glutz Motors when he got the Truckster? It was an Olds Vista Cruiser wagon. Unlike the Griswold car, though, this '72 model hasn't been crushed flat by an unscrupulous car dealer bent on selling a badly-modified Country Squire.

San Francisco Street Sighting - 1967 Oldsmobile Ninety-Eight Holiday Sedan

Oldsmobile Ninety-Eight. Not quite a Cadillac, almost a Buick. It's a puzzling place to be in the car market and in the old General Motors brand hierarchy. The Ninety-Eight was the fanciest Olds you could buy, but it was still an Oldsmobile. Even I can't figure out whether Olds or Buick was considered more prestigious in the world of middle-class luxury. You could get an Olds or Buick with the fancy vinyl roof, ornately patterned luxury interior trims, whitewall tires, script badges and convenience options similar to a Cadillac. But it would never quite be a Cadillac.

Alameda Street Sighting - 1964 Oldsmobile Jetstar 88

Few cars have carried as many marketing names as the Oldsmobile Eighty-Eight. Some have been straightforward trim levels, such as DeLuxe 88 and Super 88, but Oldsmobile has long been associated with rockets, so much so that their logo was a stylized rocket for decades. The Rocket V8 engine sparked a lineage that would include the Rocket 88, Dynamic 88, Jetstar 88, and more puzzling Delmont and Delta 88s. Delta was the most enduring nameplate, lasting more than twenty years. Jetstar, as seen here, was the cheapest full-size Olds and the name was only used from '64 to '66.

San Jose Street Sighting - 1992 Oldsmobile Custom Cruiser

I never really knew what to make of the Oldsmobile Custom Cruiser when I was younger. Well, the older ones made sense to me, the big boxy ones built between 1977 and 1990. To me, they had always been, and they were kind of cool.

Danville Street Sighting - 1948 Oldsmobile Dynamic 68

It's almost safe to say I've seen more custom cars with late-1940s Oldsmobile grilles than actual Oldsmobiles from that era. It's as if everyone scrapped them and forgot they existed. Fords, Chevys, that's all that seems to come out of the woodwork. The occasional Buick, Cadillac, Mercury or Chrysler product will pop up now and then, but Ford and Chevrolet seem to dominate the American classic car population and Oldsmobile is rarely represented. A postwar Olds, even a garden-variety four-door, is a red letter find for me.

San Francisco Street Sighting - 1963 Oldsmobile Starfire Holiday Coupe

Corporate internal competition is a funny thing. When GM wanted a piece of the burgeoning personal luxury sport coupe market in the early 1960s, they brought out the Oldsmobile Starfire to compete with the likes of the Ford Thunderbird and other sporty, two-door luxury cars. But there was a problem. See, GM's once-orderly brand hierarchy had dissolved in the interest of being all things to all people. Now they had half a dozen divisions all competing, in many cases, for the same market segment. When this Olds Starfire rolled off the assembly line in 1963, it was competing with the new '63 Pontiac Grand Prix, Buick Wildcat and sexy new Riviera. Even the higher-spec Chevy Impalas (particularly the SS) and similar Olds Dynamic 88s probably stole sales from the Starfire.

Berkeley Street Sighting - 1965 Oldsmobile Cutlass Convertible

To me, car shops are like car shows. It's not because of the one-letter difference between them, but rather because both tend to have an interesting vehicle or two parked outside on the street. Is it cheating to shoot "street sightings" there? I hope not. Some of the coolest and most historic cars eventually break and find their way to the shop to be made right again. For many, that's the only time you'll see them outside of a museum or organized car show, unless you're friends with the owner or something. I don't have that kind of connections.

San Ramon Street Sighting - 1973 Oldsmobile Delta 88 Royale Holiday sedan

Not many old cars become local celebrities. This can change, of course, if they become known for being associated with a colorful local figure or have a fascinating past, or are just distinctive enough that they attract all manner of art students and photographers who think they look cool.

Alameda Street Sighting - 1973 Oldsmobile Delta 88 Royale Holiday sedan

Rounding out this week's trio of beat-up 1970s Oldsmobiles is a 1973 Eighty-Eight Royale Holiday four-door hardtop. If you're familiar with the work of director Sam Raimi, you may know that he owns a yellow 1973 Oldsmobile Eighty-Eight sedan. The car featured rather prominently in the Spider-Man film as Uncle Ben's personal vehicle. This is not that car!
I have to ask: why aren't big family cars offered in cheerful colors like this anymore? If anything, it would give more people reason to refer to their car as the Banana Boat. There aren't many ordinary cars that wear the color yellow very well, but I actually like it on this one. Most family cars these days are beige or some greyscale tone between white and black. It's boring. Then again, the last custom-painted yellow late-model Honda Accord I saw looked stupid.

San Francisco Street Sighting - 1972 Oldsmobile Delta 88 Royale Holiday coupe

This week we're looking at early 1970s full-size Oldsmobiles in less than concours condition. As I said in my previous feature of a 1970 Ninety Eight sedan, the more luxurious-sounding the name was on these cars, the worse they tend to look now. This one is a 1972 Eighty-Eight Royale Holiday coupe.

Pleasanton Street Sighting - 1970 Oldsmobile Ninety-Eight LS Holiday sedan

I don't know what it is about vintage full-size near-luxury sedans. The more ornate their ornamentation, the more optimistic the name, the more trashed they tend to be. This one is a 1970 Ninety Eight LS (Luxury Sedan) Holiday four-door hardtop, the top model in Oldsmobile's lineup. The 98 came with a 455 Rocket V8 and was available with a host of convenience options befitting a luxury cruiser, including standard power seats, power windows, power steering and power front disc brakes, available tilt and telescoping steering wheel, 8-track tape player, and of course a luxury vinyl roof. Rear fender skirts were standard.

Best of the Rest: 1980s GM

1980 Chevrolet Citation, San Francisco

1983 Buick Century T-Type, San Francisco

1988 Oldsmobile Toronado Trofeo, San Francisco

1989 Buick LeSabre T-Type, San Francisco

1989 Cadillac Allante, San Francisco

San Francisco Street Sighting - 1964 Oldsmobile F-85 Cutlass

It's easy to note that throughout American automotive history, most buyers have favored bigger cars. Value used to be determined by how much sheetmetal you got for your dollar. Cars were advertised based on how much longer, wider and heavier they were than the competition. So you got cars like this 1964 Oldsmobile F-85 Cutlass, an "intermediate" that's the same length as a new, full-size 2011 Ford Taurus. It was bigger than earlier Cutlasses, and more powerful to compete with midsize cars like Ford's Fairlane.

San Francisco Street Sighting - 1975 Oldsmobile Cutlass 442

The bigger they are, the harder they fall. This, my friends, is an Oldsmobile Cutlass 442. It certainly looks quick, doesn't it? It has mag wheels, racing stripes, bucket seats! It must surely be a real barnstormer.

Pleasanton Street Sighting - 1977 Oldsmobile Cutlass S

One thing I have to respect is an old family car that's been kept in cherry condition, or shown the love of a proper restoration. And few have gotten a better response from me than this, a very clean
1977 Oldsmobile Cutlass S sedan.

San Francisco Street Sighting - 1958 Oldsmobile 88

1958 was an odd year for the automobile industry. Throughout the fifties, fins were in, chrome was the norm and bigger was better. But in 1958 something was different: quad headlights. Some cars wore them well (DeSoto), and some did not (Studebaker). Some have criticized the 1958 General Motors lineup of having poor styling compared to the generally good-looking (and only dual-headlight) 1957s. For sure, I wouldn't say that this '58 Oldsmobile 88 is fantastically gorgeous. Far from it. I've never been a big fan of most Olds designs from the '50s (and my favorite '58s are the Chevys and Pontiacs), but personal preferences aside, these cars have their fans.

San Francisco Street Sighting: 1961 Oldsmobile Ninety-Eight

One of the largest old cars I've seen in San Francisco (coincidentally on the same street as the '64 Porsche 356C in my previous feature) was this unrestored and mildly customized 1961 Oldsmobile Ninety-Eight (98) four-door sedan. Sporting some tasteful orange pinstriping, this must have been a classy machine in its day. That day was a long time ago, though, and today it's faded and beat-up but keeps going. Every time I've seen it, it's been parked in a different spot.

The 98's story began in 1941 with the introduction of Oldsmobile's premium full-size model, the Series 90. The two models in the 90 series were the 96 (straight-six powered) and 98 (straight-eight powered). As V8 engines became more popular in the postwar years, the 98 continued production with a V8.
This '61 Ninety-Eight appears to be the Luxury Sedan body style, which has a roofline similar to a Cadillac six-window sedan of the same era. But there, the similarities to the Cadillac end. The Olds has an entirely differently sculpted and styled body devoid of exaggerated fins. Instead, the 98 has a pointed rear end with small round taillights and a body design that resembles a rocket. Nearly everything on the car is inspired by rockets, fighter jets, turbines, air intakes, what have you. This was the sixties, after all.