Five is completely impossible. Fifty wouldn’t be enough. I’m just going to toss out some favorite songs, keep it to one song per artist (or two if splitting between a band and solo act), and keep it to basically pop/rock/R&B (no classical, old standards, or show tunes or this list would easily double) and I'm sure I'm still forgetting plenty:
Anita Mui – Don't Ask For Life
B-52's - Love Shack
The Beach Boys - California Girls
The Beatles - the long Abbey Road medley
Black Sabbath – Iron Man
Bob Dylan – Tangled Up in Blue
Cat Power – Sea of Love
Chuck Berry – Johnny B. Goode
The Cranberries - Dreams
Cyndi Lauper – Girls Just Wanna Have Fun
David Bowie – Life on Mars
The Decemberists – Sixteen Military Wives
Earth, Wind & Fire - September
Electric Light Orchestra – Mr. Blue Sky
Elton John – Goodbye Yellow Brick Road
Gnarls Barkley – Crazy
The Go-Go’s – We Got the Beat
Ike and Tina Turner – Proud Mary
In Flagranti – Pick a Trick
Jimi Hendrix – All Along the Watchtower
Joanna Newsom – Sprout and the Bean
John Lennon – Watching the Wheels
Journey – Open Arms
The Kinks – 20th Century Man
Kon-Kan – I Beg Your Pardon (I Never Promised You a Rose Garden)
The La’s – There She Goes
Led Zepplin – Stairway to Heaven
Lizzo – Truth Hurts
Lou Reed – Perfect Day
Lynyrd Skynyrd – Free Bird
Madonna – Like a Prayer
The Mamas and the Papas – California Dreamin’
Nancy Sinatra – These Boots Were Made for Walking
OOIOO – Hewa Hewa
Outkast – B.O.B. (Bombs Over Baghdad)
Paul McCartney – Maybe I’m Amazed
Paul Simon – You Can Call Me Al
Pink Floyd – Comfortably Numb
Prince – Purple Rain
Queen – Bohemian Rhapsody
Rahul Dev Burman – Mehbooba Mehbooba
The Rolling Stones – (I Can't Get No) Satisfaction
Sally Yeh – Qian Zui Yi Sheng
The Spinners – The Rubberband Man
Stereolab – Emperor Tomato Ketchup
Sukhwinder Singh & Sapna Awasthi - Chaiyya Chiayya
Sugarhill Gang – Rapper’s Delight
Van Halen - Jump
Velvet Underground – Sister Ray
The White Stripes – Seven Nation Army
