Between 1997 and 2005, the Jackson family faced some of the most trying times in their public and private lives. At the center of the storm were pop icons Michael and Janet Jackson, two siblings whose careers and personal lives were increasingly tested under the intense glare of the media spotlight.

Following the massive success of her 1995 album and greatest hits compilation, Janet Jackson signed a groundbreaking $80 million deal with Virgin Records in January 1996. The four-album contract marked her as the world’s highest-paid entertainer at the time. Unlike previous years, Michael Jackson—whose stardom often eclipsed even the brightest stars—was no longer overshadowing Janet’s accomplishments. Janet had established herself as a consistent hitmaker and performer, adapting to new trends while keeping her unique star quality intact.

By the late 1990s, Michael’s musical relevance was more a tribute to his legacy than to current success. His infrequent public appearances and controversies starkly contrasted Janet’s active engagement with youth culture through music, collaborations, and roles in blockbuster films.

In 2001, both Jacksons released new albums—Michael’s Invincible and Janet’s All For You. Janet’s image transformation into a confident, sexually liberated single woman was embraced, with her album going multi-platinum and launching a successful tour. Michael’s album, despite his legendary status, faltered amidst disputes with Sony and a shift in public perception.

The early 2000s brought greater turmoil for Michael. The infamous 2003 Living with Michael Jackson documentary by Martin Bashir reignited long-standing suspicions about his relationships with children. That same year, he was formally charged with multiple counts of child molestation and intoxicating a minor, setting the stage for a high-profile trial.

Janet, trying to avoid entanglement in her brother’s controversies, kept a low profile until early 2004 when she agreed to perform at the Super Bowl halftime show. What was intended as a career-defining performance turned into a cultural flashpoint. During a duet with Justin Timberlake, a planned costume reveal went awry, exposing Janet’s breast to a live audience of over 90 million viewers.

The backlash was immediate and severe. While Timberlake walked away with little damage to his reputation, Janet became a target of public outrage. The FCC imposed heavy fines, networks banned her content, and conservative pundits decried the performance as moral decay. Unfairly linked to her brother’s legal battles, Janet’s career took a significant hit.

Despite the controversy, Janet released her album Damita Jo in 2004. The record, drenched in sensual themes, faced widespread censorship and limited promotion. The media’s fixation on the Super Bowl incident overshadowed her music entirely. MTV and radio stations distanced themselves, and Janet was effectively blacklisted in many spaces where she had once thrived.

As Michael’s trial commenced in early 2005, Janet shifted her focus to supporting her family. She stood in solidarity with Michael, appearing at court with her siblings in coordinated white outfits—symbols of peace, innocence, and resilience. The trial’s emotional toll was immense. Janet later revealed she had experienced depression during this period, overwhelmed by the dual backlash against both her and her brother.

When Michael was acquitted on all charges in June 2005, the relief was bittersweet. The Jackson family’s public image had been deeply scarred. Janet, accepting a humanitarian award later that year, declined to joke about the past events, stating, “My family and I have just gone through the least humorous chapter of our lives.”

Between public scandal and private pain, the Jacksons weathered a storm few could comprehend. Though the world saw two of pop’s biggest stars under pressure, what remained unseen was the emotional weight carried behind the cameras. This period remains one of the darkest and most defining in the legacy of both Michael and Janet Jackson.