I'm not a huge music fan; most of what I know comes from the radio.
Here are ten random songs, in approximately chronological order:
The Mamas and the Papas - "California Dreamin'"
Diana Ross and the Supremes - "You Keep Me Hanging On"
Simon and Garfunkel - "Cecilia"
Bonnie Tyler - "Total Eclipse of the Heart"
Madonna - "Borderline"
The B-52's - "Love Shack"
The Red Hot Chili Peppers - "Under the Bridge"
Ricky Martin - "Livin' la Vida Loca"
Green Day - "Holiday"
Gnarls Barkley - "Crazy"
In no particular order
"You Have More Friends Than You Know"
"The Sound of Silence"
"Happy Together"
"Stabat Mater" (by Dvorak; first and last movements)
"O, Holy Night"
"You'll Never Walk Alone"
"Bridge Over Troubled Water"
"I'll Make Love To You"
"Sit Down, You're Rockin' the Boat"
Title song from "Mame"
Mark, thank you for making my list look just a little less dated.