Off the Pickle Boat

Greg in New York, New York, says that when he looked a bit disheveled, his mother would say You look like Willie off the pickle boat. The phrase goes at least as far back as the 1890s, and the proper name has varied. The person on the pickle boat has been, among others, Annie, Molly, Charlie, and Chauncey. Among those who race seacraft, a pickle boat is slang the last boat to arrive. This is part of a complete episode.

Transcript of “Off the Pickle Boat”

Hi there. You have A Way with Words.

Hi. This is Gregory Millar from New York.

Hey, Gregory from New York, New York.

New York, New York. Yeah. So nice. They named it twice. Yep.

Welcome to the show. What can we do for you?

My mother used to use an expression often when I was a kid,

And it’s Willie off the pickle boat, she used to say.

I think it had a lot of different meanings,

But I think one of the meetings was like you looked a little disheveled or straighten your tie or comb your hair a little bit better.

But it might have had some other meetings as well, so I never really knew who Willie was, what a pickleboat was, what the whole thing meant.

So I thought you might be able to help me out with that.

You looked like Willie off the pickleboat.

Yeah, she would say I looked like Willie off the pickleboat.

So how long ago were we talking about here?

So my older siblings probably would have heard this phrase in the 1950s and 60s, and I heard it more in the late 60s, early 70s.

Okay, yeah, that sounds about right.

Well, Greg, the thing with this expression, it goes back to at least the 1890s, but the name has changed on it.

You can find Willie is sometimes Annie, sometimes Charlie, sometimes Molly.

The first name that I find is Chauncey.

And I think Willie kind of became the firm popular favorite because there was a song at least as early as 1912 called Willie Off the Pickle Boat.

And I don’t have the lyrics for that.

I think the song fixed that name.

And the song is of no real import.

You can find lyrics and variety of different versions of it out there on YouTube or wherever.

But I think if you look at the Smithsonian Folkways collection, you’ll find a version by Ella Jenkins, which is pretty good.

But I don’t know why Willie was on the pickle boat, but I do know why it was called the pickle boat.

At least I’m pretty sure.

And I think Martha agrees with me on this one.

When there’s a boat race, particularly a yacht race, the last one in is called the pickle boat.

So it’s the loser in a boat race.

And so it’s kind of this position you don’t want to be in really unglamorous.

You’re the slowpoke.

You’re the slowpoke.

And the joke sometimes is that the reason it’s called the pickleboat is because you stopped.

You’re so slow, you must have stopped to do some fishing and to pickle the fish before coming ashore.

Oh, okay.

So that’s the reason that you lost the race.

So anyway, yeah, so somebody who’s really off the pickle boat is naive or unsophisticated or disheveled or a rube or disreputable.

There’s always something kind of negative and undesirable about them.

Okay.

So you’re saying this was not a compliment?

No.

No.

Not at all.

I’m sure your mother loved you, but not when she said that.

Okay.

Got it.

Got it.

Okay.

Well, I’m glad I’m straight on that.

Yeah.

I was actually thinking, too, that my association with the Willie part was Steamboat Willie, because it was a boat, and Mickey Mouse was on the boat.

So that’s what I always thought.

Yeah, what year was that? Was it the 1920s that that film came out?

In the 20s, yeah, yeah.

But it all makes sense, because her mother, my mother’s mother, and my mother’s father, they were born in the 1890s, and my grandmother went to college during World War I.

So that might have been a song that was popular, like when she was in high school.

So I’m sure that my mother got it from her mother or her father.

So that timing makes sense, too.

Well, there you go.

Yeah, excellent.

Excellent.

That’s good to know.

Well, we appreciate your calling.

Yeah, yeah.

Well, thanks very much.

I’m glad I got that straight.

Thanks, Greg.

Take care.

Okay.

Thanks a lot.

Bye-bye.

Bye-bye.

Bye-bye.

Bye.

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