1. The Replacements
"Unsatisfied"
A jangly standout from the band's 1984 classic Let It Be, equal parts punk, folk and blues. "Paul Westerberg rocks," says Jewel. "His lyrics are beautiful and so starkly simple, they break your heart."

2. Ella Fitzgerald
"Love for Sale"
The First Lady of Song offers a stunning, saucy take on Cole Porter's standard. "It's sung from the perspective of a prostitute, and it just paints such a specific picture, the listener is carried away."

3. Bruce Springsteen
"The Ghost of Tom Joad"
Jewel finds the sunny side of Springsteen's bleak Steinbeck-inspired protest song. "I always think of this record for driving and watching the sun come up."

4. James Blunt
"You're Beautiful"
The U.K. singer's tale of love across the subway tracks ends sadly: "It's time to face the truth/I will never be with you," which suits Jewel just fine. "I think it's really pretty."

5. Tammy Wynette
"They Call It Making Love"
Someone send our Alaskan friend a copy of the country crooner's Just Tammy album. "I heard it over the speakers at a supermarket, but I haven't been able to find the song anywhere. I would remake it."

Listen to the playlist