But in the eighth year, the spell was broken.
On Sunday, "Colbert" marked the end of an era when the series took that top honor, providing a boon to its 49-year-old host and the deadpan character he's created.
"[I]t's sort of a cliche to say that it is such an honor just to be nominated, but it's more than that. It's also a lie," Colbert quipped as he took to the Nokia Theatre L.A. Live stage with writers and others who work on his show.
The win ended a streak that actually began in 2003, when Stewart's "The Daily Show" won the first of 10 straight awards in the category. It also provided a student-has-become-the-master moment for Colbert, who came to prominence on Stewart's program and who in the early years of the "Report" (pronounced "ruh-poor," of course), benefited greatly from his Comedy Central lead-in.
If he felt the baton had been passed, though, Colbert wasn't letting on.
"Jon Stewart's streak is not broken. He is an [executive producer] on the show. So he's won for the 11th time. Congratulations, Jon," Colbert told reporters backstage. "The Colbert Report" also picked up the win for writing in a variety series, the third time it's won the prize. (Stewart's "The Daily Show" has won eight times.)
Emmy wins in the Variety category tend to come in bunches. Before "The Daily Show's" run began in 2003, "Late Show With David Letterman" won five in a row. "The Tonight Show," "The Carol Burnett Show" and "Saturday Night Live" had also won multiple times.
The wins over the last decade for Comedy Central — a relatively small cable operation run out of New York — suggested a sign-of-the-times shift from an era when broadcast dominated the category.
The "Report" was created in 2005 as a way of extending the "Daily Show" brand with Colbert, at the time a popular correspondent on the fake-news program.
His character, also named Stephen Colbert, is a faux conservative modeled on right-wing cable-news hosts a la Bill O'Reilly and Sean Hannity. In satirizing them, Colbert has become a touchstone of sorts for the left.
The Colbert character also interacts with real-world events off-camera—he famously attempted a run for presidency in 2008--and, on the show, interviews guests with his signature brand of outsized narcissism. As Colbert took the stage Sunday, he said, "I personally have to thank my friend and my brother, Jon Stewart, who is the one who said, 'We should do a show together where you are a professional idiot.'"
But Colbert also offered a shout-out to a less heralded inspiration. "We get a boost," he said backstage, "from just how stupid the real news is."
Yvonne Villarreal contributed to this report.