Songfacts®:

• Every small town has its local legends, the folks people tell stories about for generations. In John Mellencamp's stomping grounds of Seymour, Indiana, these were two guys who were best friends, always up to something. In the song, he changed their names to Theo and Weird Henry, but they were based on those two real people, who you could often find dancing on the roof of a van with their shirts wide open.
  
  Of course, these days don't last forever, and eventually Theo and Henry moved on. But that moment in time they shared together was truly magical.
• David Masciotra, author of Mellencamp: American Troubadour, pegs "Theo And Weird Henry" as a hidden gem in the Mellencamp catalog. "It's a great song and it has a really killer arrangement," he said on the Songfacts Podcast. "The interplay between guitar and violin, and Kenny Aronoff plays a spectacular drum part, as he always did. Mellencamp's vocal on it is really effectual and moving. It's one of the most beautiful tributes to friendship that I've ever heard in song. It's like a Larry McMurtry story put to music, and he's able to capture this special feeling of insider status that close friends have amongst each other, like you're the only one in the world who understands each other. It always made me think of my best friend growing up. For various reasons, I'm not in touch with that guy, so now it's a very sad song for me to hear. When I told Mellencamp that, he said that the two guys who he named Theo and Weird Henry - those weren't their actual names - they're both deceased now, so it's become a very sad song for him as well."
• This is an album cut from Big Daddy, Mellencamp's last LP of the '80s. Many pop stars were evolving their sound to keep up with the trends (dance tunes and power ballads), but Mellencamp didn't want to be a pop singer, as he declared on the album's first single, so he moved more toward roots music with his sound. His popularity leveled off, but the album and his next four all sold over a million copies.
• The line, "Called themselves the 'He-man women-lovers club,'" is a reference to a bit on The Little Rascals TV series. The young boys on the show formed the "He-man women-haters club."