By Daniel D'Addario
Updated: August 4, 2015 3:20 PM ET | Originally published: February 11, 2015

Jon Stewart is receiving a great deal of praise for his work as the host of The Daily Show, the Comedy Central program he’s hosted since 1999 and from which he retires on Thursday. While Stewart’s biting wit and timely commentary have come in for celebration, Stewart had a few stumbling blocks: Some small, some substantial.

Surely Stewart’s replacement, Trevor Noah, will have high expectations thrust upon him— but it’s worth remembering that Stewart, like any host, wasn’t perfect.

John Yoo: For someone who was so good at holding people to account when they weren’t in-studio, Stewart tended to waffle when those with whom he disagreed were in front of him. He apologized to his viewers for his interview of John Yoo, the Bush administration lawyer known for his forceful advocacy of torture. “He slipped through my fingers,” Stewart said of Yoo after a 2010 interview widely seen as a long string of over-the-plate softballs, in which Yoo calmly explained what he saw as torture and not torture with little pushback. Years later, Stewart would still be astounded by torture defenders, but a moment when he had one in the studio was utterly unproductive.

The Daily Show
Get More: Daily Show Full Episodes,Indecision Political Humor,The Daily Show on Facebook

Condoleezza Rice: Stewart’s apology was unusual, but the soft interview style wasn’t. In 2011, Condoleezza Rice defended the Iraq War on Stewart’s show with little real contradiction from Stewart. Her defending her own administration’s decisions is predictable enough, but someone who’d risen to fame on the back of his comic opposition to those decisions defaulting to deference was confusing. Why have interviews at all if when faced with those you most harshly critique through comedy, you cede the floor to them?

The Daily Show
Get More: Daily Show Full Episodes,Indecision Political Humor,The Daily Show on Facebook

Hugh Grant: All that said, Stewart cannot necessarily be blamed for being a congenitally bad interviewer. His worst moment may not have involved any political figures at all; he’s said his experience with Hugh Grant was so negative that he’ll never have Grant back on the program. Grant himself said his “inner crab” came out on the 2009 appearance. (Ironically enough, in an earlier era of his career, Grant is credited with helping to turn around Jay Leno’s fortunes with a heavily-hyped appearance on The Tonight Show.) The interview is strangely tense and uncomfortable; Grant clearly didn’t come to play, and Stewart seems at a loss.

The Daily Show
Get More: Daily Show Full Episodes,The Daily Show on Facebook,Daily Show Video Archive

Accent work: Every late-night host, by dint of having to spend so much time on the air, develops tics. Consider Conan O’Brien’s “string dance,” or Johnny Carson pretending to swing a golf club, or everything about Jay Leno. But Jon Stewart’s preferences were higher-decibel. It’s hard to pick out the single moment at which Stewart’s interest in absurdist accents came to overtake his satirical point-of-view, but it grew exhausting keeping up with someone so very excited about the possibility of pretending to be an Italian mobster, or a Jewish mother, or a gay man, and so very not-great at actually doing the voices. This compilation gives a good sense of Stewart, the Man of One Very Loud Voice.

The Daily Show
Get More: Daily Show Full Episodes,Indecision Political Humor,The Daily Show on Facebook

Rally to Restore Sanity: For all Stewart’s flaws, he was a hugely influential broadcaster. But the direction of that influence sometimes seemed muddled. He went to the trouble of throwing, with Stephen Colbert, a rally in 2010 — one that is rarely mentioned nowadays, not least because its central idea was an equivalence between the far left and the far right (both sides were equally involved in ruining the tone of the national discourse!) that wasn’t borne out by the events of the years that followed. When asked in interviews, before and after, what exactly he thought was wrong with America, Stewart would say, in some form or another, that he was “only a comedian.” Right: A comedian who could catalyze huge gatherings of people with his ideas, which he then avoided owning up to. Stewart’s big idea, as his show aged, seemed to be that it was easier to throw one’s hands up and bemoan all politicians as completely crazy without getting into specifics, because that’s not what a comedian does. But it’s a nihilist attitude that’s informed politics, and arguably made them worse.

Contact us at editors@time.com.

SPONSORED FINANCIAL CONTENT

Read More From TIME

EDIT POST