Curbside Jukebox: 1969 Oldsmobile Ninety-Eight Convertible – If You Should Sail

1969 Oldsmobile Ninety-Eight convertible. Rogers Park, Chicago, Illinois. Sunday, May 5, 2019.

This isn’t my first time professing my love for so-called yacht rock, and it won’t be the last.  I have a complicated relationship with the song by the Nielsen/Pearson Band after which I have subtitled this essay.  Sonically, it’s flawless as an example of this kind of soft rock that was first popular for roughly a decade, starting around the mid-’70s.  Lyrically, it could be seen either as an overture from a hopeless romantic who professes continued and undying love toward an ambivalent object or, alternately, sung from the perspective of an ex who just refuses to let go.  More on that in a second, but there are several tie-ins in my mind between “If You Should Sail”, this convertible, and the area in which I spotted it.  Loyola-Leone Beach Park in the Rogers Park neighborhood is rich with nautical flavor, with many sailboats present on nearby Lake Michigan during warm summer days.

Loyola-Leone Beach Park.  Sunday, October 17, 2021.

I had just left the nearby Lighthouse Tavern (also nautically themed, naturally) on a Sunday four years ago and was waiting for the bus, when this Ninety-Eight convertible came cruising northbound on North Sheridan Road.  One of my favorite things to do at the Lighthouse was to load up the jukebox with many of my favorite hits of yesteryear, and many great discussions would then ensue with friends and other bar patrons.  Our ages and backgrounds ranged as widely as the thoughts and associations many of those songs elicited.

In my vast mental music library, I have tended to pick out songs to play that have had limited mainstream exposure since when they were first released or were popular.  Tunes that haven’t been referenced as much in popular culture in other contexts usually end up feeling more closely tied to their specific moment in time, versus songs that have been brought back for commercials and the like.  “If You Should Sail” is an example of the former, the only Top-40 hit on the Billboard Hot 100 chart for the Nielsen/Pearson duo.  It peaked at No. 38 in November of 1980.

Some sample lyrics:

You can get behind the wheel
And drive your heart out
Take that Oldsmobile
And stake your claim
Just to find all that runnin’s in vain
And it will remain the same

If you should sail upon a ship
I’m gonna stow away
And if the ocean’s wide
Baby it’ll take a long while
If you should sail out on a trip
Over your shoulder cast an eye
I’ll be there wearing a smile

1969 Oldsmobile Ninety-Eight convertible. Rogers Park, Chicago, Illinois. Sunday, May 5, 2019.

I have a few thoughts, immediately.  The trunk of this Ninety-Eight convertible definitely looks large enough for an adult-sized stowaway.  There’d be the safety issue of the car not having an interior trunk release, but I’m sure if a person was desperate enough to stalk someone by hiding in the trunk of their car, they probably would have thought about a plan to get out.  Also, the female love object of the protagonist might have been driving an Oldsmobile, but it wouldn’t be a then-eleven-year-old Ninety-Eight.  She would have been driving a Cutlass Supreme (or Supreme Brougham) like a gazillion other United States citizens.

Those lyrics are something, though.  That guy was in love, or really obsessed.  Obsession is not a form of love, and hopefully most people realize it.  I can’t imagine anyone, male or female, being turned on by advances like that, but the song just goes down so smoothly that I can’t help but bop my head to it.  I’m still really happy when the shuffle algorithm lands on it.

1969 Oldsmobile Ninety-Eight convertible. Rogers Park, Chicago, Illinois. Sunday, May 5, 2019.

And my, is this car beautiful.  The ’69 model year was the penultimate one for the Ninety-Eight convertible, with the Delta 88 continuing through ’75 as the last, full-sized Oldsmobile soft-top.  Just under 4,300 open-air Ninety-Eights found buyers that year, with another 3,200 or so sold in 1970 before the final curtain came down.  That 4,300 figure represented less than 4% of total ’69 Ninety-Eight production of 116,400.  Clearly, new-car buyers of the day were over the convertible by the late ’60s, especially as a choice in a luxury automobile.

1966 Oldsmobile Ninety-Eight sales brochure page, as sourced from

There was just one engine in any ’69 Ninety-Eight, and that was a big, 455-cubic inch Olds Rocket V8 with 365 horsepower and 510-lb ft of torque, mated to a three-speed Turbo Hydramatic transmission.  I remember this car gliding through the intersection as if buoyant and forging its way through water’s resistance.  The Oldsmobile “rocket” imagery synonymous with its brand doesn’t exactly fit this car, but I don’t think it really has to.  The point of a big, powerful engine in a huge car like this (224.4″ long, 80″ wide) isn’t to win any races, but to ensure smooth, comfortable, no-nonsense cruising with no doubts in the driver’s mind as to its capability to handle what it needs to, provided he or she can afford the fuel costs.

You can change your name
Change your address, too
Play that runnin’ game
It’s nothin’ new
Try to hide for all the good it will do
You know it’s true

1969 Oldsmobile Ninety-Eight convertible. Rogers Park, Chicago, Illinois. Sunday, May 5, 2019.

Nope.  That’s called stalking, though it really is too bad Oldsmobile’s buying clientele didn’t sustain a similar level of devotion and tenacity to the brand before it disappeared in 2004.  Of course by then, there was nothing in Olds showrooms approaching the kind of ostentatious, over-the-top character as this Ninety-Eight convertible, save for maybe the first Aurora that appeared for ’95.  I wonder sometimes how the drivers of the cars I stop to photograph feel about some guy on the sidewalk snapping pictures as they drive by.

As has been previously discussed at Curbside in the comments, I think most drivers behind the wheel of an interesting car would appreciate someone else’s attention to it, and I certainly hope that’s how the owners feel about the cars I choose to feature here.  It’s never my intent to seem like a paparazzo or like I’m following someone.  “I’ll be there wearing a smile” is the last line in the chorus of “If You Should Sail”, which seems to be a fitting end to both my essay and also how I felt on that warm Cinco de Mayo immediately after spotting this fine Ninety-Eight.

Rogers Park, Chicago, Illinois.
Sunday, May 5, 2019.

“If You Should Sail” lyrics by Mark Pearson and Reed Nielsen.

Brochure page as sourced from