By the time he ended his run as host of The Late Late Show in December 2014, Craig Ferguson had hosted more than 2,000 episodes produced over the course of a decade. Yet when asked to name the worst guest he’d ever had to deal with, he didn’t even need to think about it before answering. Keep reading to learn who gave Ferguson his hardest day on the job, and why you’ll be hard-pressed to discover exactly why.
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Ferguson waited until his show was ending to name his worst guest.
The Scottish comedian and host dropped the name of his most troublesome guest while talking to another television host, Andy Cohen, during an appearance on Watch What Happens Live that originally aired on Bravo in September 2014. Just months earlier, Ferguson had announced plans to close out his tenure on The Late Late Show at the end of that year.
The revelation came during the show’s rapid-fire “Plead the Fifth” segment, during which interviewees are challenged to a lightning round of tough questions. They can either answer them or choose to or “plead the fifth.” When asked to name the worst guest who ever appeared on his show, Ferguson hesitated only briefly before naming Macy Gray—the R&B singer who rose to fame with her massively popular 1999 debut album On How Life Is, which included the hit single “I Try.”
Gray appeared on The Late Late Show on Oct. 10, 2005, and the episode apparently stuck in Ferguson’s memory for all the wrong reasons.
“I think she was in a bad mood that night,” Ferguson told Cohen. "I don’t think she’s a bad person.”
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The episode came early in Ferguson’s tenure.
Albert L. Ortega/Getty ImagesRather than lay the blame at the feet of his guest, Ferguson was quick to accept some measure of responsibility for the bad interview, noting that he was “very new” in his hosting gig at the time. Gray’s October 2005 appearance came less than a year after Ferguson took over as host of The Late Late Show in January, as he was still settling into the grind of late-night television.
“I couldn’t handle it [then],” Ferguson told Cohen. “I think now it would be OK.”
You can’t find the interview online.
Erika Goldring/Getty ImagesThough many interviews from Ferguson's era of The Late Late Show live on in perpetuity on the internet, his interview with Gray is impossible to track down online, so it’s difficult to say if it would seem to have gone as poorly to viewers today as it did to the host back in 2005. (There is a video on YouTube of Gray performing her song “Real Love” on the episode, though Ferguson does not appear in the clip.)
The inability to judge the interview itself against Ferguson’s later recollections has frustrated fans for decades, at least according to the comments below Ferguson’s appearance on Watch What Happens Live. They are filled with commenters searching in vain for the controversial Gray clip.
“SOMEONE FIND THAT MACY GRAY INTERVIEW!” a user commented in 2015. “It's now been more than four years [since the Watch What Happens Live interview] and I've still never seen that Macy Gray interview,” commented another in 2019. “Still. Looking,” said another in 2022.
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Gray caused controversy with a recent talk show appearance, too.
Gregg DeGuire/WireImageWhile whatever frustrated Ferguson about Gray’s appearance on his show has been lost to time, much more readily available are comments the singer made in a more recent interview that drew much more significant criticism.
In the summer of 2022, the singer made an appearance on Piers Morgan Uncensored to discuss an op-ed she’d written suggesting “the American flag no longer represents democracy and freedom.” During the interview segment, the conversation turned to the rights of transgender Americans, and the singer shared provoking, bigoted statements about transgender women. A week later, Gray made a public apology for the comments while appearing on Today, telling host Hoda Kotb she had “learned a lot” since her discussion with Morgan.
“I never meant to hurt anybody. I think it takes a lot of courage to be yourself. Anyone who is in the LGBTQ community is a hero,” Grey said on Today, as recounted by Vanity Fair. “I said some things that didn’t go over well but my intention was never to hurt anybody. I feel bad that I did hurt some people and I think it’s about education, conversation and us getting to a place where we understand each other.”
