The cover of 2006's Out100 issue mixed LGBTQ+ trailblazers with fierce allies, featuring Michael Kors, Anne Hathaway, John Cameron Mitchell, Iman, and Rufus Wainwright.

Brokeback Mountainhad come out at the end of the previous year, making a major impact at the subsequent Academy Awards, leading the nominations with eight nods and tying with three other films for most wins (four). More than that, it became a rare film centering queer stories that penetrated the mainstream — although in later years, it would also come to be an example of both how these stories are so often left in the hands of heterosexual creatives and how the general public, at the time, only seemed able to embrace LGBTQ+ films steeped in tragedy.

Still, it was Brokeback Mountain's year, playing a role in Hathaway's appearance on the cover. By that point, the actress had already proven her talent for switching between comedic roles like in The Princess Diaries and more serious fare — Havoc had already done the film festival circuit. With the release of The Devil Wears Prada in the summer of 2006, Hathaway seemed well on her way to being beloved by the gays.

Although she was already engaged with activism and charity work, it was in the years that followed that she became an outspoken LGBTQ+ ally, raising money to support marriage equality and pushing back against discriminatory laws.

"I don’t consider myself just an ally to the LGBT community, I consider myself your family," she said in 2008, a decade before she would be honored by the Human Rights Campaign for her allyship. "And so, I’m doing what we should all do with our families — I’m loving you, I support you, I completely accept you as you are, as I hope you do me, and if anyone ever tries to hurt you, I’m going to give them hell."

Mitchell released a film in 2006 that pushed boundaries in a different way. His follow-up to Hedwig and the Angry Inch, Shortbus, was an erotic exploration of human connection, featuring a number of queer and sexually fluid characters. It was controversial at the time, due in part to including a number of unsimulated sex scenes, and remains controversial to this day — in 2022, it was reported that Prime Video had rejected the film several times over "offensive content."

However, Mitchell's own career has continued on. In addition to directing two more feature films, his acting career has seen him featured in productions such as Girls, The Sandman, and Joe vs. Carole. Hedwig was revived for a short run on Broadway in 2014, even winning a Tony for Best Revival of a Musical.

Also in 2006, Michael Kors was continuing to make waves in both the fashion world and with his charity work. His work with a group focused on providing meals to sick people, including those with HIV/AIDS, had been ongoing since the 1990s, and would eventually culminate in God's Love We Deliver opening in the Michael Kors Building in New York in 2015.

Fashion model and cover star Iman was similarly hard at work drawing attention to important causes. That year, she co-hosted a benefit to raise funds to support communities impacted by HIV/AIDS in Africa and India, alongside husband David Bowie, Alicia Keys, Wanda Sykes, and others. She was later appointed the charity's Global Ambassador as she continued to raise awareness of the crisis, particularly as it affected her homeland of Somalia.

Wainwright's appearance on the December 2006 cover of Out was his second in conjunction with the Out100 list. He had released three more albums since his 1998 debut by then, and had blown fans away with his recreation of Judy Garland's famous 1961 concert at Carnegie Hall that summer. The tribute was so successful that the singer went on to perform it four more times in Europe and Los Angeles the following year before releasing an album, Rufus Does Judy at Carnegie Hall, of the live recordings at the end of 2007.