The late singer, a 13-time Grammy winner, passed away in May 1998 at the age of 82. The unexpected resurgence of 'Jingle Bells' on the Hot 100 dated December 23 is a testament to the enduring appeal of Sinatra's iconic voice and timeless recordings. 'Jingle Bells' has soared to the 20th position on this year's Billboard Hot 100, marking his fourth entry into the Top 20 and his first since 1967.