"My Way" is still one of my best received songs at Senior and Nursing facilities. It's all in the presentation. If you sing it with confidence, and conviction - it's not sad, at all.
Plus one for My Way.
The only thing I no longer say is the line I was using that Frank used at the 1974 Main Event performance at Madison Square Garden. Sinatra before singing "My Way " said and We Will now do the National Anthem but you need not rise, he then segued into the song. I once did that at an assisted living facility and despite saying "no need to rise" a couple of people did. If I close with that song now I usually say "now Frank Sinatra's national anthem.