Aside from chuckling again at the irony of old Bunker, nearing 60 at the time, chiming in on Madonna, I got a big kick out of one of the lines that precedes it, spoken by the dearly-departed Chris Penn, forever to be remembered by the masses as "Sean Penn's little brother." But, the man was a fine actor in his own right, as anyone who sees him in Short Cuts, The Funeral, Reservoir Dogs, and any number of his other numerous roles can attest to. Even being a longtime fan of Sean Penn, I somehow never caught, or had forgotten, the in-joke that Tarantino fit into the scene for Chris Penn to play off. When Tim Roth's Mr. Orange reveals that he is unfamiliar with Madonna's "True Blue," Penn's Nice Guy Eddie replies incredulously, "Oh, you ain't heard "True Blue"? It was a big-ass hit for Madonna. I don't even follow that Top 10 pop shit, and even I've heard of "True Blue.""
I knew that this song was written and released in the middle of Sean and Madonna's tempestuous relationship and I figured this might have been one of the ones written "for Sean." Sure enough, upon checking that most trustworthy source, Wikipedia, my hunch was confirmed. Not only the song, but the entire album of the same name, was dedicated to Sean, "the coolest guy in the universe." Now, I'm wondering how Sean, not known for his sense of humor, felt about his brother poking a little fun, at his (then recent) ex-wife and the song characterized as an "unabashed valentine" to him.
Original paparrazzo Ron Galella snapped a thinner than thin Christopher Penn and his date (and Wild Life co-star) Sherilyn Fenn at a May 24, 1984 production of Nine.