Billy's Holiday is a 1995 Australian musical film, directed by Richard Wherrett and starring Max Cullen.

As the film begins, bus driver Sid (Drew Forsythe) is stuck in traffic on King Street, Newtown, making light of the situation by playing "I Can't Get Started" on trumpet to his passengers.

He is dating a woman named Kate (Kris McQuade), but is going through a period of indecision and inertia in life as he recovers from his divorce from Louise (Tina Bursill).

Meanwhile, Kate's friend Julie (Genevieve Lemon) has lately been studying Ancient Egyptian afterlife beliefs and the possibility of "soul reincarnation".

One night, after Billy sings "After You've Gone" in a gruff voice at a local bar, Julie leads a séance at a yum cha restaurant which hypnotises those around the table.

His daughter Casey is again embarrassed in front of her friends as they witness Billy recreate Gene Kelly's "Singin' in the Rain" dance on their street, but this moment leads to a discussion between them about his newly-awakened emotional state.

When Billy sings "What a Night, What a Moon, What a Boy", it leads both Julie and Kate to call his sexuality and gender identity into question.

At one stage he hallucinates a vision of himself in the mirror wearing a fruit hat à la Carmen Miranda and remarks, "Strange...

Walking through an empty train station, he sings "I Had Too Much to Love Last Time" in a more refined version of his original voice as Kate listens on.

He receives a standing ovation as the spirit of Holiday watches on approvingly from the back of the audience, blowing a kiss and then walking away.

Billy then visits Kate at her hairdressing job the next day, offering her a rose and singing "I'll Do Beautiful Things to Your Heart".

The play debuted in 1980 at Sydney's King O'Malley Theatre, with Max Cullen in the role of showbiz reporter Leo Coote.

[1] Wherrett picked up the project as he was drawn to the premise of "a middle-aged man getting a second chance at life and love", and later connected this to his diagnosis as HIV positive.

This 25-second sequence required the cameraman to walk backwards down the bus with a steadicam, then step onto a giant cherry picker which lifted into the air.

[8] Wherrett never returned to filmmaking after Billy's Holiday, but directed several more stage productions and worked on the opening ceremony of the Sydney 2000 Olympics before his death in 2001.

James Morrison played trumpet, including the opening rendition of "I Can't Get Started" in the style of Bunny Berigan.

"[11] Paul Byrnes called the film "a folly of substantial proportions (that) dies a thousand deaths before it's over", but spoke highly of the "heartfelt and true" scene in which Cullen sings "Am I Blue?

[14] One positive review came from Arizona Republic's Bob Fenster, who called the film "a sly sendup of the music business (that) will make you want to sing and dance up and down the aisles".