Having broken through to popular success with Night Songs, Cinderella returned with their second album, Long Cold Winter, in July 1988. Radio initially focused on the track "Gypsy Road," giving it a Top 20 ranking in the Album Rock Tracks chart, but Mercury did not release it as a single at first (although in the U.K., where it was released as a single, it charted). Instead the power allad &"Don't Know What You Got (Till It's Gone)" was released as a single in August, and it peaked at number 12 in November. The album reached number ten in September, the same month it was certified gold and platinum simultaneously, with a double-platinum certification following in November. (It was certified triple platinum in January 1997.) As the group continued to tour relentlessly through 1988 and 1989, Mercury broke more singles from the LP. "The Last Mile," released in December, peaked at number 36 in March 1989; "Coming Home," released in March, hit number 20 in June; and "Gypsy Road," finally put on 45 a year after the release of Long Cold Winter in July 1989, and backed by a live version of the Rolling Stones' &"Jumpin' Jack Flash," got to number 51 in September.

Again, Cinderella came off the road and spent a year crafting its third album, Heartbreak Station, which appeared in November 1990. Although it was a hit out of the box, going gold in January 1991 and platinum in February, the album encountered more resistance than the band's previous efforts, peaking at number 19, with no multi-platinum certifications forthcoming. Leadoff single "Shelter Me" peaked at number 36 in February, and the title song reached number 44 in April. More disturbing than this mild commercial disappointment, however, were problems within the band. Coury departed, and Cinderella initially replaced him with Kevin Valentine, then hired noted session drummer Kenny Aronoff temporarily before bringing in Kevin Conway. Then, after the U.S. leg of the Heartbreak Station tour had ended and the band was gearing up to go to Japan in 1991, Keifer woke up one morning and found he couldn't sing. Doctors initially were unable to figure out what was wrong, but a specialist finally diagnosed paresis of the laryngeal nerve controlling the left vocal cord. Keifer was forced to undergo two throat operations, followed by extensive therapy. Cinderella managed to put a track, "Hot and Bothered," on the chart-topping Wayne's World soundtrack, released in February 1992, but otherwise the band was out of commission for an extended period of time.

In the meanwhile, fashions changed. Cinderella had been part of a "pop-metal" movement including Bon Jovi, Great White, and Ratt, who preceded them, as well as Poison, the enormously popular Guns N' Roses, and L.A. Guns, who followed them. But when "grunge" rockers Nirvana, boasting a neo-punk style, broke through to success in the fall of 1991 with their album Nevermind and single "Smells Like Teen Spirit," the record labels suddenly became enamored of their stripped-down approach. Suddenly, instead of the teased and blown-dry coiffures and skin-tight stage costumes of the pop-metal bands, it was the dirty-hair-falling-in-the-face, flannel-shirt-and-jeans look of Nirvana frontman Kurt Cobain that was all the rage. Soon, the pop-metal groups were written off with a new epithet, dismissed as "hair metal" bands. By the time Keifer & Co. finally emerged with the fourth Cinderella album, Still Climbing, in November 1994, it could only manage to spend one week at number 178 before disappearing. Mercury promptly dropped the band.

Cinderella's touring opportunities also dried up, and while the group did not formally disband in 1995, it became inactive for lack of offers. Keifer moved to Nashville in 1997 and worked on his songwriting, eventually getting cuts on albums by Andy Griggs and Lynyrd Skynyrd. By 1998, there was enough interest by promoters for Cinderella to reunite (with Coury rejoining) for a tour. On October 2 and 3, they appeared at the Key Club in Hollywood, CA, and recorded the show for an album, Live at the Key Club, released on Cleopatra's Dead Line label in July 1999. Unfortunately, the disc was also licensed out to other labels over the years and has confused consumers by also appearing under the titles In Concert and Live From the Gypsy Road. Meanwhile, Cinderella had been signed to Sony's Portrait label by famed record executive John David Kalodner, who was also signing other hard rock bands of the '80s. But initial Portrait releases were not successful, and Cinderella's contract was canceled. Nevertheless, a faithful fan base supported continuing road work by the band, which reunited in the summer of 2000 for a tour with Poison, followed by a second outing by the two groups in 2002. In 2005, VH1 sponsored the Rock Never Stops package tour, which Cinderella headlined, supported by Ratt, Quiet Riot, and Firehouse, with dates extending through the summer. ~ William Ruhlmann, All Music Guide