Tiffany's second studio album, Hold an Old Friend's Hand, featured a Top 10 single which charted on the Billboard 200 in 1988.

Two additional releases from Tiffany, 1990's New Inside and the Asia-exclusive Dreams Never Die in 1993, both failed to rekindle significant interest.

[7][8] Tiffany began singing at age four when she learned the words to the Tanya Tucker song "Delta Dawn".

[13] Tiffany set a record for the youngest female artist to top the Billboard charts with a debut album.

In 1988, at the peak of her popularity, Tiffany was embroiled in a conflict in which Tobin fought her mother and stepfather over control of her career and earnings.

This was rejected by the court, but the judge did allow her to move out of her mother's home, and her grandmother (who sided with Tiffany during the trial) became her temporary guardian.

Tiffany's career suffered as musical tastes changed in the early 1990s, moving away from dance-pop and towards harder-edged rock and rap.

[20] Her third studio album, the urban-influenced New Inside (1990), received mixed reviews from music critics,[21] and failed to chart, despite several TV appearances to promote it, including on the fantasy sitcom Out of This World.

[22] During a brief early 1990s comeback attempt, Tiffany reunited with Tobin on the album Dreams Never Die (1993), which spawned the singles "If Love is Blind" and "Can't You See".

[23] In 1995, Tiffany moved to Nashville to develop her career as a songwriter, and to attempt a return as a country music artist.

[27] Tiffany stated in interviews that she explained to her nine-year-old son that it was no different from posing in Vogue or Elle, except that it showed more.

[27] She added years later that while she had no regrets about posing in Playboy, some of her family members disapproved because of how young her son was at the time.

In March 2008, Tiffany released Mimi's Kitchen, an album limited to 500 copies and featuring rare demos from age three through the present.

The song consisted of Tiffany performing vocals for the dance team Hydra Productions; it is on their album Liquid.

In late July 2008, a new Tiffany dance song remixed by Dave Audé, "Just Another Day", was released on CD.

[citation needed] On October 18, 2008, Tiffany appeared on the CMT reality show Hulk Hogan's Celebrity Championship Wrestling, and was eliminated in the first episode.

On April 22, 2011, it was announced that Tiffany would be teaming up with fellow 1980s pop music sensation Debbie Gibson for an upcoming summer concert tour titled Journey Through the 80's.

[31] In December 2012, having opened a clothing boutique of her own, Tiffany appeared on TLC's makeover reality show What Not to Wear.

[39] In October 2019, Tiffany was a featured guest on The Sam T. Blues Revue, the successor of The BluesMobile Radio Hour.

"Angels" was written and recorded at her home studio in Nashville, Tennessee with Mark Alberici and Margie Hauser.

[42] Tiffany then addressed the event herself, apologizing for her actions that she claimed were the result of a combination of voice loss, panic attack, and frustration.

[43] Tiffany's eleventh studio album, Shadows, produced by Alberici, was released on November 25, 2022[44] via Deko Entertainment[45] and Revolt Artist Management.

[47] Some controversy resulted from the fact that Janet Waldo, who had voiced the character in all previous Jetsons material, had all of her recorded dialogue in the movie replaced[48][49] because studio executives thought Tiffany would attract a younger audience.

Also in April 2008, Tiffany made a cameo appearance on the sitcom How I Met Your Mother in the episode "Sandcastles in the Sand".

She played herself as a backing vocalist in the 1980s-inspired music video by a fictional teen Canadian pop star who was inspired by real-life singers like Tiffany making a career out of performing in malls.

In the film, she plays Karen, a fun-loving adrenaline junkie who takes matters into her own hands after a blizzard traps her and her friends in a cabin, when paranoia gets the best of them.

Tiffany's musical contemporary, Debbie Gibson, had her film Mega Shark Versus Giant Octopus premiere at Cannes, as well.

[53] Tiffany and Gibson starred together in a Syfy original movie Mega Python vs. Gatoroid, which aired January 29, 2011.

[57] On the episode first broadcast July 7, 2013, of the reality TV series Celebrity Wife Swap, she traded places with actress/singer Nia Peeples.

Later that year she starred in a Miracle Whip commercial alongside other celebrities, including Wynonna Judd, Lance Bass, Susan Boyle, and the Village People.