That Time Stephen Colbert Lost To Barry Manilow At The 2006 Emmys

Following the highly successful inaugural season of his own show, The Colbert Report, former Daily Show correspondent Stephen Colbert found his new show nominated for several Primetime Emmy Awards in 2006. The Colbert Report was up for four awards in the Variety, Music, or Comedy Program category — Outstanding Directing, Outstanding Individual Performance, Outstanding Writing and Outstanding Series. Of these, Colbert’s name was attached to the latter three, but only one of them was solely his to win or lose.

Colbert lost the Outstanding Individual Performance in a Variety or Music Program to Barry Manilow. Yes, that Barry Manilow. The guy whose songs regularly pop up on your parents’ favorite Spotify playlists. The category was stacked against Colbert from the start; the other nominees included David Letterman, Craig Ferguson, and Hugh Jackman (who has claws for hands). But Manilow? Really? Surely his nomination was simply the Television Academy’s way of giving the singer a pat on the back.

Yet when Tracy Morgan and Tina Fey presented the award during the Emmys telecast, the winner’s name rhymed with “Marry Banilow.” Mr. “Copacabana” himself stuttered when he took the stage, saying he couldn’t “be more surprised” at his win. Little did the live audience and the viewers at home know that Colbert, along with some assistance from Daily Show host Jon Stewart, had prepared for this very moment.

“This is about the Manilow thing.”

Colbert and Stewart came onstage later in the telecast to present the Emmy for Outstanding Reality-Competition Program. The Amazing Race won, but nearly a decade on, no one who was watching remembers this.

“Thank you very much,” said Stewart. “It’s a pleasure to be here tonight.”

“Good evening, godless sodomites,” followed Colbert, much to the crowd’s delight.

What followed was a hilarious back-and-forth in which the sore loser heightened his Colbert Report persona. While Stewart coyly mocked the awards program, especially the particular category he was presenting, his partner ridiculed the Emmys and everyone watching. Then, after the Colbert’s “kneel before your god, Babylon!” outburst, Stewart turned to his former correspondent and uttered the six best words of the night: “This is about the Manilow thing.”

“I lost to Barry Manilow!” Colbert exclaimed, and the audience lost it. Subsequent shots of Jeffrey Tambor, John Lithgow, Warren Beatty and other performers revealed faces red with laughter and wet with tears. It was, without a doubt, the best 30 seconds of the entire Emmys telecast.

“I’m the real winner.”

Colbert then insured his loss to Manilow, as well as The Colbert Report‘s losses in the three other categories, would not soon be forgotten. The comedian milked it for every possible ounce of comedy. When the show returned after a brief hiatus on Sept. 11, 2006, the host made sure to address the golden statue-sized elephant in the room.

“I could not be more proud,” he gestured to the hissing crowd. “After all, before the ceremony I made my prediction to Ryan Seacrest on E!”

In the clip from the E! red carpet pre-show, Seacrest opined that Colbert “oughtta at least get one” of the three Emmys he was nominated for. Colbert disagreed, saying: “I don’t think so. This is Manilow’s night!”

“I said it folks, and I was right,” he then told the Colbert Report studio audience. “So, Nation, I called it!”

With Manilow’s hit song “Copacabana” playing over the loudspeakers, dozens of red, white and blue balloons dropped onto Colbert’s desk while he danced in his chair, reveling in the presumed success of having predicted Manilow’s Emmy win — albeit at his own expense.

“Now the way I see it, since Barry didn’t know that Barry would win, and I knew that Barry would win, I’m the real winner,” he concludes, before sadly noting that the trophy’s sharp wings would have popped his balloons. Such was the first of many indications that Colbert’s latest feud would be with his Emmy rival, and that it wouldn’t be over any time soon.

“Can we get the notary please?”

Nearly two months later, the Oct. 30, 2006 episode of The Colbert Report finally brought the entertainers’ faux feud to a head. The titular host did what he could to prepare the studio audience for the singer’s arrival, but the real fireworks began when the two sat down together over at Colbert’s interview table.

The bit began with Colbert showing off his 2005 and 2006 Emmys (from his time as a writer on The Daily Show), 2004 Peabody Award (also from his Daily Show work), and a glass-placeholder-thingy from Time for his inclusion in their 2006 Time 100 list. From that point on, the two didn’t waste any time trading comedic jabs.

However, the pièce de résistance of the whole affair came during the second half of the interview, when Colbert asked his Emmy-winning rival: “Who do I pay off to win next year?”

Manilow feigned ignorance, saying that he wouldn’t have anything to enter into the 59th Primetime Emmy Awards. Then he argued that Colbert would “get it next year,” saying that the show host was “so young!” That was all Colbert needed to proceed to the gag’s logical conclusion — a peace treaty between the two men, to be read, agreed upon, and signed at the end of the interview. In doing so, Manilow agreed to “joint custody of the Emmy” and suggested the two men share it “every six months.” There was a notary public on hand to notarize the document, rendering a legally-binding peace agreement between Colbert and Manilow.

The singer then signed an amazing decorative plate for Colbert’s sister, Margo…

…then stuck around to serenade the Colbert Report audience with a tune.

The series finale of The Colbert Report aired on Dec. 18, 2014 — over eight years after the signing of the Stephen Colbert/Barry Manilow Peace Accord. Naturally, Manilow was one of the many guests Colbert invited to the taping.

“I was told that Stephen had chosen only his favorite guests,” he told The Desert Sun, the paper-of-record in Palm Springs, California. “I couldn’t have been more honored to be included in that stellar group.” Manilow joined almost 100 other famous guests who gathered to send Colbert off with a stirring rendition of “We’ll Meet Again.”

While Manilow hasn’t been invited to the Late Show with Stephen Colbert yet, it’s sure to happen at some point. Besides, it looks like the Ed Sullivan Theater is now the hottest spot north of Havana.