The first exposure to Der Bingle was when I was 2, Disney had separated some of their half hour shorts from the 40s on VHS. I had 'Mickey and the Beanstalk', but the trailers before the main program showed clips from the others including 'The Legend Of Sleepy Hollow'. I was entertained by the Ichabod song and wanted to watch it, but alas I never did. A few years later I was helping my mother put up Christmas decorations, and we had on a TV that played Christmas music, and Bing's 'Frosty the Snowman' came up. I remember initially judging it as I loved Jimmy Durante's version of 'Frosty'. I would encounter his Christmas music from time to time after that and watched Holiday Inn and White Christmas with my family.
About 10 years after hearing him sing 'Frosty', as a Christmas fanatic, I decided to find a few free Christmas albums on Amazon Prime music, and I greatly enjoyed what I heard. Around this same time my parents and I were trying to find music I liked besides Christmas music. I didn't like modern stuff or Elvis, I tried Frank Sinatra and he just didn't grab my attention. I grew to like some of Frank's Christmas outings as well as Bing's, so a picked up 2 Christmas CDs of theirs. A Laserlight mostly radio CD of Bing, and a Columbia Christmas Compilation for Frank. Another year went by and I got a few more CDs, mainly of Bing, The Complete Decca Christmas Songbook and the Christmas TV Specials, Volume 2 of the the Television Specials. At the time I didn't realize I was buying duplicates. I listened to the CDs and decided to look for some non-Christmas outings by Bing, and enjoyed them. I then bought a import 2CD set from Amazon called 'The Very Best Of Bing Crosby' and loved it. Later on that spring I decided to buy my first load of regular Crosby stuff (not counting the 2CD set mentioned), ordering multiple records and the His Legendary Years set. From then on I was a set-in-stone Crosby fan.
To help keep his legacy alive I've introduced him to many of my friends both at school and online. This has made a few more people Crosby fans. One tip I will give is to, if you have children, have your children, if they like Crosby, tell their friends about him. I know I was glad to find his music...