I love oldies.
I am sure you have listened to the beatles/rolling stones stuff, but some people haven’t heard much beach boys and bob dylan. The beach boys Pet Sounds album is great. You can look for both of those.
For Bob Dylan (not sure how old some of them are) - Mr. Tambourine man, Hurricane, Tangled Up in Blue, Blowing in the Wind, Shelter from the Storm, Mr. Bojangles, Masters of War, Times they are a’ changing, Rolling Stone
For Beach Boys - God Only Knows, Sloop John B, good Vibrations, In my Room, Don’t Worry Baby, Help Me Rhonda, Heroes and Villains (newer, but one of their best songs)
Some specific songs off the top of my head
Patsy Cline - Crazy (The all-time best country song. I have yet to meet anyone who doesn’t like it even those that don’t like country.)
The Crew Cuts - sh-boom (Have you ever seen the movie clue? If so you’d recognize this.)
Elvis Presley - Love me Tender (All girls love elvis don’t they?)
Mickey and Sylvia - Love is Strange (Also on the dirty dancing soundtrack.)
Other bands off the top of my head
Herman Hermits, Velvet Underground, Bing Crosby, Louis Armstrong, BB King, Aretha Franklin, Ella Fitzgerald, Nat King Cole, Willie Nelson, Simon and Garfunkle,