Tell Me Where I'm Going (Wrong)
Jul 21, 2026 · 47 min · 9 segments
This week Josh and Sean discuss Madonna's famous "Italians do it better" T-shirt. How did this tee become so iconic? It only appeared in one music video but went on to become forever linked to the pop…
Josh LeunerHost
And also like to a, to a Madonna fan of our generation, it's such an obvious reference, isn't it? Like it's straight away, you know exactly what it is, but it's weird.

And yet it, for some reason it has, it sort of became this mythical image of her, like this, this timeless image of her, but I would love to know why she chose that.

But yeah, I think younger people, even Madonna fans, may not really know what the reference is.
No, I don't think so because I see people who are self-professed Madonna fans online who are of younger generations and they react to songs that, to me, are part of her mainstream canon.

And also like to a, to a Madonna fan of our generation, it's such an obvious reference, isn't it? Like it's straight away, you know exactly what it is, but it's weird.

And yet it, for some reason it has, it sort of became this mythical image of her, like this, this timeless image of her, but I would love to know why she chose that.

But yeah, I think younger people, even Madonna fans, may not really know what the reference is.
No, I don't think so because I see people who are self-professed Madonna fans online who are of younger generations and they react to songs that, to me, are part of her mainstream canon.
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