Anastacia is marking the 25th anniversary of her breakthrough album Not That Kind with an extended tour and has been recounting moments from her pre‑fame years, including one in which Arnold Schwarzenegger asked her to sing En Vogue’s "Whatta Man" a dozen times.
The Chicago‑born singer said the silver‑anniversary schedule — more than 70 dates across 2025 and into 2026 — has brought new and younger audiences to shows that originally drew fans with the 2000 hit "I'm Outta Love." The single was a Top 10 hit in 19 countries and the album went on to sell more than four million copies worldwide.
Anastacia described a long period of singing at corporate events and private parties before her television breakthrough on MTV’s talent show The Cut in 1998, when her distinctive voice and stage presence generated immediate industry interest. "When they first see me, they just think I'm four eyes and blonde hair," she told viewers at the time. "When I sing, it's very different." Michael Jackson reportedly phoned to try to sign her after that TV appearance.
She recalled being frequently hired for high‑profile functions before commercial chart success, including singing at Steven Spielberg’s wedding and other celebrity events. "I played Arnold Schwarzenegger's birthday, and he had me do En Vogue's 'Whatta Man'," she said. "I think I sang it 12 times." The anecdote underscores a lengthy period when she earned her living performing repeatedly at private engagements while record companies debated how to market her.
Her TV moment led to a record deal and the release of Not That Kind at the turn of the millennium. Anastacia was 32 when she made her debut album, though early press materials understated her age. The album's mix of soul, pop and rock stylings and her raspy, powerful voice earned widespread international success even as she struggled to break into the U.S. market.
Anastacia has said she was effectively blacklisted from play on two major American radio stations at the start of her career, a situation that hindered her ability to promote songs in the U.S. and chart on the Billboard lists. "To this day, Anastacia has never troubled the US Billboard charts," she said in recounting how that early setback limited touring options and left her initially unable to mount a viable U.S. tour. It was not until her third album, 2004's Anastacia, that she embarked on the 80‑date "Live At Last" tour across Europe, including performances at Wembley Arena and large outdoor shows.
Her career has included personal setbacks and comebacks. Anastacia has survived breast cancer twice and has said optimism helped sustain her through periods when record companies considered her "un‑signable" because of her look and voice. Her medically prescribed color‑correcting glasses, worn since childhood, have become a visual trademark; she has said the glasses are necessary so she can see at a distance.
Social media has renewed interest in her catalogue. Anastacia noted that "Left Outside Alone" has now eclipsed "I'm Outta Love" in some online popularity metrics, while other tracks such as "Paid My Dues" are receiving fresh attention. That renewed engagement has dovetailed with the anniversary tour, bringing older fans and a wave of younger concertgoers who missed her first run of dates.
Looking ahead, Anastacia said she plans to return to the studio after the tour to work on two new albums but did not set release dates. "After all these years, the music industry is still a mystery," she said, noting conflicting pressures to take time while also meeting fast turnaround expectations.
Across a career that has ranged from corporate gigs and celebrity parties to arena tours and benefit concerts, Anastacia’s account highlights how an unconventional voice and image, early radio setbacks in the U.S., and personal health battles have been woven into a still‑active international career. The silver‑anniversary tour has given the singer a chance to reintroduce those songs to new audiences while she prepares fresh material.