Random five! Described!

1. The Modern Jazz Quartet - Milano. Named after my second favorite Pepperidge Farm cookie, because of the way the chocolatey middle is just a little too thin and the cookies are a little too dry.
2. Led Zeppelin - You Shook Me. Written by Gladys Messner the morning after the great San Francisco earthquake of 1952. Her bird, which normally both whistled and sang the whole day long, was mysteriously silent the day before the quake. This alerted Mrs Messner to the upcoming tremblor, at least subconsciously, and so she took an extra sleeping pill that evening, leaving her dazed and blissfully confused, while she shook all night long.
3. Tortoise - Cornpone Brunch. Originally a children's song used by teachers to teach the days of the week, it was reworked by Tortoise, on commission, into the background music for the slide show at a local bank's semi-annual half-day conference and leadership seminar.
4. Vampire Weekend - Everlasting Arms. The Everlasting Arms is a prison in the west of Scotland, permanent home to the worst criminals the northern UK can produce. Bloody Face, from the entertaining-but-crazy second season of American Horror Story, is reportedly based on one of the inmates held there.
5. Benny Goodman Trio - At Sundown. This song does not actually exist (which you can confirm for yourself by searching for it on YouTube). It was added to the disc's playlist as a copyright trap after a rash of bootleg Benny Goodman albums nearly destroyed the market. Sounds like every other mid-tempo Benny Goodman tune.

Are you up to the task?