The very American song "What Made Milwaukee Famous" was never a big hit in the US, but Rod Stewart made it famous in the UK.

Nelly's "Country Grammar" is a celebration of his hometown of St. Louis, which some folks from the coasts consider "country" because it's in the Midwest.
The TV show Cheers was nearly canceled after its first season, but the theme song, "Where Everybody Knows Your Name," was very popular. To satisfy viewer demand, the theme was made into a full song and released as a single.

Mickey Mantle and John Madden both appear in the video for "Me And Julio Down By The Schoolyard" by Paul Simon. Biz Markie and Big Daddy Kane do a rap intro.

The Simon & Garfunkel song "Mrs. Robinson" was originally called "Mrs. Roosevelt," most likely after First Lady Eleanor Roosevelt. The title was changed when it was considered for use in the film The Graduate, where Anne Bancroft's character is Mrs. Robinson.

"Stuck In The Middle With You" by Stealers Wheel was the unlikely choice for a scene in Quentin Tarantino's 1992 movie Reservoir Dogs where somebody loses an ear.
The lead singer of Everclear, Art is also their primary songwriter.
Gary Lewis and the Playboys had seven Top 10 hits despite competition from The Beatles. Gary talks about the hits, his famous father, and getting drafted.
A popular contemporary folk singer, Williams still remembers the sticky note that changed her life in college.
The renown Texas songwriter has been at it for 40 years, with tales to tell about The Flatlanders and The Clash - that's Joe's Tex-Mex on "Should I Stay or Should I Go?"
When a song describes a wedding, it's rarely something to celebrate - with one big exception.
Meshell Ndegeocello talks about recording "Wild Night" with John Mellencamp, and explains why she shied away from the spotlight.