Old Man Time

This seems appropriate for New Year's Eve—Louis Armstrong and Jimmy Durante singing "Old Man Time".

(You Make Me Feel Like) A Natural Woman

Aretha Franklin performing "(You Make Me Feel Like) A Natural Woman" for the Carole King tribute at this year's Kennedy Center Honors.

The Song's Gotta Come From The Heart

Frank Sinatra and Jimmy Durante performing "The Song's Gotta Come From The Heart".

Breaking Up Christmas

Fiddler Tommy Jarrell performing "Breaking Up Christmas".

Hello

From Postmodern Jukebox, Maiya Sykes performing Adele's "Hello" in the style of a late 60's soul song.

That's All

Sister Rosette Tharpe and Band performing "That's All".

The Sound of Silence

This is the final #1 song from 1965. From 50 years ago, Simon & Garfunkel performing "The Sound of Silence".

Christmas (Baby Please Come Home)

Even though the tradition ended last year, I still can't give it up. So here is Darlene Love's first performance of "Christmas (Baby Please Come Home)" on The Letterman Show in 1986. Not quite the lavish production it became in later years.

River

Joni Mitchell and Herbie Hancock performing Joni's song "River".

Christmas With John Prine

Two John Prine covers—Amos Lee's cover of "Christmas in Prison" and Jolee Patkai's cover of "Silent Night All Day Long".

In the Bleak Midwinter

This seems like an appropriate song for the winter solstice. Chrissie Hynde with the Blind Boys of Alabama performing "In the Bleak Midwinter", based on a poem by Christina Rossetti in response to a request from the magazine Scribner's Monthly for a Christmas poem.
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Christmas Guitar Spectacular

Four guitar videos for Christmas: 

Trace Bundy 



Al Di Meola



Leo Kottke



Phil Keaggy

Hark, I Hear the Harps Eternal

The Reinhardt University Concert Choir performing "Hark, I Hear the Harps Eternal".

Édith Piaf - 100

To mark Édith Piaf's 100 birthday (12/19/1915) here she is performing "Padam Padam" (Lyric Translation)

Over and Over

The number one single from 50 years ago, "Over & Over' by the Dave Clark Five.

Sometimes I Cry

Chris Stapleton's performance of "Sometimes I Cry" on the Tonight Show.

Sweet Bells

Kate Rusby performing "Sweet Bells" with a brass band.

Boots of Spanish Leather

Bob Dylan's song "Boots of Spanish Leather" performed by Mandolin Orange.

I Saw Three Ships A Sailing

Marianne Faithful and The Chieftains performing "I Saw Three Ships A Sailing".

Hard Candy Christmas

Cyndi Lauper covering Dolly Parton's "Hard Candy Christmas".

Heart of Gold

James Taylor covering Neil Young's "Heart of Gold".

Over In The Gloryland

Shotgun Jazz Band with—as you might guess—a jazzy version of "Over In The Gloryland". Not the way Ralph Stanley does it, but great all the same.

8 Days Of Hanukkah

Sharon Jones and the Dap Kings performing "8 Days Of Hanukkah".

Frank Sinatra - 100

Frank Sinatra was born 100 years ago today (December 12, 1915). Here is Old Blue Eyes when he was still quite young, performing "Night and Day" in the 1943 film Reveille With Beverly.

Who Says

John Mayer performs an acoustic version of "Who Says".

Magnolia

Elizabeth Cook covering the JJ Cale song "Magnolia".

A Song For You

Leon Russell's "A Song For You" performed by pianist Herbie Hancock and jazz vocalist Gregory Porter with Vince Mendoza conducting the Los Angeles Philharmonic at the Hollywood Bowl, Los Angeles, CA August 6, 2014.

Hobo's Lullaby

The Wainwright Sisters—Martha and Lucy—performing "Hobo's Lullaby".

Trio

Linda Ronstadt, Dolly Parton and Emmylou Harris perform a trio of songs from the Trio album:

• "Those Memories of You"
• "To Know Him Is to Love Him"
• "Hobo's Meditation"

I Sing Because

Forever Redeemed performing "I Sing Because".

Everybody Knows

Leonard Cohen performing "Everybody Knows".

Leaving Louisiana in the Broad Daylight

Emmylou Harris and Rodney Crowell performing "Leaving Louisiana in the Broad Daylight".

Richland Woman Blues

Maria Muldaur and the Jim Kweskin Jug Band performing "Richland Woman Blues".

To Love Somebody

Lizz Wright covering the Bee Gees' song "To Love Somebody".