The Appointments of Dennis Jennings - Steven Wright - 1988

Air Date - HBO 1988

The Appointments of Dennis Jennings is a
1988 American short comedy film, starring and co-written by Steven
Wright, which won the Academy Award for Live Action Short Film at the
61st Academy Awards in 1988.

Dennis Jennings is an introverted
daydreamer, sleepwalking through life. He is a professional waiter and
has an equally-dull girlfriend, Emma. In an attempt to release his
pent-up feelings of isolation, he begins seeing a psychiatrist, only to
discover that the doctor is somewhat less than interested in what he has
to say. After finding his doctor sharing his intimate secrets with a
group of fellow psychiatrists at a bar, he then learns the doctor has a
another more unprofessional involvement in his life.
- Written by J. L. Travers