Maybe you've seen this one:
Original "Twilight Zone" TV episode dated 1960 titled "Mr. Bevis", starring Orson Bean as an eccentric young man (the title character) quite down on his luck but high on life with a fun-loving, child-like attitude.
Along comes a guardian angel, played by Henry Jones, who reverses the young man's fortunes; getting him a good job, good money, good clothes, and a place to live, albeit, a very routine and boring existence.
The deal-breaker comes, however, when Bevis discovers,
"Hey! Where's my Rickenbacker?!!"
"No, no. No Rickenbacker," scolds Jones, "That was part of your OLD life."
In the final scene, we see the young man shuffle out into the street, laughingly-attired, penniless, and recently evicted but grinning ear-to-ear as he cranks up his dilapidated 1924 Rickenbacker, gets in, and chugs off into the sunset. (sigh)