"Leaving on a Jet Plane" (1971)
John Denver's melancholic ballad about hitting the road and leaving behind his loved one (a hit for Peter, Paul & Mary) sounds like it was written for Sinatra, even if it wasn't. The sense of road weariness heard in "Both Sides Now" is even more ingrained here: You can hear in Sinatra's voice all the years of touring, sleeping in hotels and hanging out in dressing rooms. Except for a splash of brass in the chorus, the arrangement mostly restraints itself. One of the highlights of Sinatra's pop period.