Word Association Wednesday: The Double Dare

 

For this week’s Word Association Wednesday, we’re springboarding off Sunday’s Double Check Stomp and following the word double straight into one of 1938’s most irresistible pop confections: I Double Dare You. It’s one of those songs that seemed to be everywhere at once in the late ’30s - a perfect blend of bounce, flirtation, and that lightly sassy wink that defined so much of the era’s dance music.

And if we’re talking I Double Dare You, there’s only one place to start.

Larry Clinton and Bea Wain

Let me just say it plainly: Larry Clinton is the most underrated bandleader of the Swing Era. The man had taste, polish, and a knack for arrangements that were both danceable and musically satisfying. He wasn’t flashy, he wasn’t gimmicky - he was just good, consistently and quietly good, in a way that history tends to overlook.

And then there’s Bea Wain, my favorite big‑band “canary” of them all. She had that rare combination of warmth, clarity, and rhythmic poise - never overselling, never underplaying, always landing right in the pocket. On I Double Dare You, she’s at her absolute best: bright, confident, and just teasing enough to make the title feel like a promise.

Let’s spin their Victor record:

The Clinton/Wain version is the hit for a reason. It’s crisp, buoyant, and utterly charming — the kind of record that makes you understand why 1938 dancers kept dropping nickels into jukeboxes.

Satchmo Doubles Down

For contrast, we hop over to Decca for Louis Armstrong’s take, recorded in January of 1938 — just weeks after Larry Clinton had already put his version in the can at the tail end of ’37. Clinton’s record hit the market first, but Armstrong wasn’t far behind, and the two versions ended up circulating side by side through most of 1938.

At this point in time, Decca often paired Louis with then‑current pop material to keep him in the mainstream ear. His I Double Dare You sits alongside other pop covers that he transformed into Armstrong vehicles through sheer personality.

It’s fascinating how the same tune can wear two completely different suits: Clinton’s is pressed and tailored; Armstrong’s is relaxed and lived‑in. Both work. Both swing. Both show how flexible a good pop tune could be in the hands of musicians who knew exactly what to do with it.

A curious footnote: Even though Terry Shand was currently leading a band and had just come off a stint as singer–pianist with Freddy Martin’s orchestra, neither he nor Martin seem to have ever recorded I Double Dare You!

Which One Wins?

Depends on your mood. If you want polish, charm, and the best canary in the business, Clinton and Wain take the crown. If you want personality, grit, and that unmistakable Armstrong joie de vivre, Decca’s your stop.

Either way, “I Double Dare You” proves that a simple word - double - can open the door to a whole little corner of 1938 worth revisiting.