Here are three personal picks that came to mind: First,
Paul Hardcastle, the song
"19". With it's English techno beat, the effort fits the mid 80s while the lyrics recall the 60s. And yet, it's an unsettling fit for 2003-2009.
In a much lighter mood: A little ditty not about Jack and Diane, but Jimmy and Mary-Anne.
The Looking Glass offered this as the follow-up to their smash hit, Brandy (You're A Fine Girl.) Read the bio on The Looking Glass and Brandy. Note the legendary Buffalo air personality who should be in the Buffalo Broadcasters Hall of Fame.
Chart-wise, Jimmy Loves Mary-Anne wasn't anywhere near the song that Brandy was, but it has a terrific jazz guitar groove on the intro (14 seconds for the talk-up in case you're rehearsing) and the Hammond B-3 in the bridge is absolutely major market. The lead singer's voice on the opening lines is as smooth as Johnson's Baby Oil on a baby's butt.
From the CanCon
way back machine (thanks to Don Berns with an "e" for stiring this category) I nominate The Ungly Ducklings,
"Gaslight", a song that was all over 1050 CHUM back in the day. There's plenty of power on the intro and lots of grit from the male vocalist who also has great range. And if you listen closely, check the arrangement of the strings under the powerful refrain. Producers and arrangers don't get anywhere near the credit they deserve.