Made in 1994 Staring: Rik Mayall (I’ll put up the rest of the cast-list as soon as I can find my copy)
A really really weird made for TV movie. It stars with a few middle-age men, playing cowboys in (if I recall) an abandoned car lot. The protagonist works at some dead end job and spends all his free time trying to write the Great Cowboy Novel. After an argument with his neighbor over propriety lines, the neighbor wife throws a pot at him from the upstairs window. This plunges him into a movie-long fantasy sequence, in which he is the sheriff of a standard wild west town. Highlights include a cosmetic obsessed Wyatt Earp, the musical Billy The Kid and Jessie James, and an Indian from India. For the last little bit, it suddenly goes into a modern gritty inner city setting.
It is only about an hour long. And yes, as the name suggests, it does have a lot of singing (most of the dialog is sung). I advise you to check it out (good luck finding a copy though, the only one I have is about 7 years old and taped off TV). It’s one of the ones you either love or hate (I am the only person I know who likes it, and I really like it); Very weird, and very imaginative.