Serenading Miss Daisy: The Old Folks at Home

It's well documented that our brains store different types of memories in different places. This is clearly evident in the elderly; an octogenarian who may not remember his last name, can still sing along to a tune he hasn't heard in 50 years. It isn't a mere reflexive response, the listener knows what's being played and enjoys it.
In the case of my mother, 84 years old, it has been something of a challenge to find what she listened to, way back when. When I was a kid her tastes had taken on a pious hue, but today, those songs don't appeal to her very much. I remember her telling me about the way they got music when she was a kid: the gramophone & Victrola (78's, 16's, and even wax cylinders), the crystal radio (that she and her sisters called "the hear"), and further along, on a table radio (an Atwater Kent - later repossessed in the Great Depression), but I don't recall her telling me what she listened to on those ancient machines. I probably wasn't paying close attention. To make things even worse, she liked a lot of the music that her mother (born 1890) and her grandmother (born 1855) liked. I had a lot of ground to cover.
A couple of years ago I found a diary she kept as a child and it was full of references to Bing Crosby, so I bought her a Bing Crosby CD and sure enough, she started singing right along. Recently we were watching a documentary about the Carter Family and I was pleasantly surprised to hear her singing along with those songs too. I never expected that, but I remember my aunt once told me "your mother liked hillbilly music when she was a kid." I never quite knew what she meant, until that documentary came along.
Some of the songs from the past are considered objectionable today, especially around young ears, but with all the recording options now available, we can edit those songs out. If your elder likes Stephen Foster, just leave in "Oh Susannah" and leave out "Old Black Joe." You never know what some people will object to: I remember my very Conservative brother-in-law's irritation over his 4 year old having picked up an old song titled "You Ain't Done Nothin' if You Ain't Been Called a Red." I guess it was the poor grammar that bothered him.
There are contemporary musicians who dip into the old songbook on a regular basis. I recommend anything by Leon Redbone or Jim Kweskin. My mom loves those guys. And sometimes, what your elder disliked back then, is now a favorite; my mother didn't care for Frank Sinatra and Tony Bennett before, but she likes them now. One more note: It doesn't always work by sitting the person down alone in a room with the music, try playing it in the car or in the background. Oh, and never, ever assume they can work the machine that's playing the songs.

Here are some CD's my mom likes, maybe your mom, or grandma, or great-grandmother, will like them too:

Bing Crosby: 16 Most Requested Songs

Leon Redbone: On the Track

Jim Kweskin: Side by Side

Penthouse Serenade: Nat King Cole at the Piano

The Carter Family: Best Of , Greatest Hits

Swanee: The Music of Stephen Foster

Maria Muldaur: On the Sunny Side