The subject for Day 8 of my 30 Day Song Challenge is “A song to drive to late at night“, and the first song I thought of was “I Drove All Night” by Cyndi Lauper. (A runner-up was the beautiful Cars song “Drive”, but Cyndi Lauper’s 1989 hit is a no-brainer for this subject.) The song was a sizable hit for Lauper, reaching #6 on the Billboard Hot 100, #7 in the UK and #8 in Canada. She had a string of hits from 1984-89, beginning with “Girls Just Want to Have Fun”, and two of them – “Time After Time” and “True Colors” went all the way to #1. “I Drove All Night” was her last single to reach the top 10 in the U.S.

The song was originally written by Billy Steinberg and Tom Kelly for Roy Orbison, who recorded it in 1987, a year before his death, but his version was not released until 1992. Lauper recorded the song and released it as a single in April 1989. She liked the song and wanted to record her version because she liked the idea “of a woman driving, of a woman in control.” I love the strong propulsive rhythms, blasting drumbeats and edgy strings that powerfully convey the passion and urgency of a woman driving all night to get to her lover. And I really like Lauper’s vocals, which have a somewhat more mature quality than on some of her earlier songs.

The song was included on her third studio album A Night to Remember, and considered by nearly everyone to be the highlight of an otherwise disappointing album. A Night to Remember received mixed-to-poor reviews and less commercial success than her two previous albums. Because of its poor reviews and disappointing sales, as well as the problems she experienced with producer and boyfriend David Wolf⁠ during the production of the album, Lauper referred to it as “A Night to Forget”. Despite the album’s poor performance, “I Drove All Night” was nominated for a Grammy for Best Female Rock Vocal Performance.

The song was also later covered by Celine Dion in 2003, whose version topped the Canadian Singles Chart and reached #7 on the Billboard Adult Contemporary chart.

Here’s Roy Orbison’s original version, which is also pretty good. The song’s official video features the young and very beautiful actors Jennifer Connelly and Jason Priestly.