The Best And Worst Moments From White House Correspondents Dinner Hosts

The White House Correspondent's Dinner is an annual event that brings together members of the media and political heavyweights in Washington, D.C. for a night of comedy and fun. The event is often hosted by a comedian, which ensures that the jokes told that night will be memorable at the very least.

The upcoming annual dinner, scheduled for April 30, will mark the first time a sitting President has attended since 2016, when former President Donald Trump opted to stop going. The event itself hasn't happened in two years owing to the ongoing pandemic, but the 2022 dinner will return in person and will be hosted by Trevor Noah. The president of the White House Correspondents Association told USA Today they are looking forward to Noah's performance, saying, "Trevor is an incredible talent who keeps us laughing — and thinking — four nights a week. We can't wait for him to help bring our 100-year Washington tradition 'Back to Abnormal.'"

Noah will be taking the stage after years and years of comedians who have come before him. Here are a few of the most memorable performances from past White House Correspondents Dinners.

Comedian and "Community" star Joel McHale hosted the annual dinner in 2014 and definitely didn't do as well as he might have hoped. As The Wrap reported at the time, most of his jokes fell pretty flat and ended up unnerving the crowd more than they entertained. McHale went after a plethora of concerns and features about others, including mocking the supposed intelligence level of Jessica Simpson and poking fun at former New Jersey Governor Chris Christie's weight.

Many of the people who were at the butt of the jokes weren't too surprised by their content. As Christie told USA Today, the jabs at his size and weight were funny ... kind of. "They were great," he apparently said without much enthusiasm. "About what I expected."

In fact, if anyone got praise for their jokes that night it was then-President Obama. Both The Wrap and USA Today noted that attendees and the press alike enjoyed the former leader's jokes, even if McHale himself was a bit of a disappointment.  

When comedian Paula Poundstone hosted the White House Correspondent's Dinner in 1992, she was determined not to make her sex the focus of the evening. As she later told Elle, "I work in a business where there is a smaller percentage of women than there are men. But I never think too much about gender — never did." Instead, Poundstone plugged away, coming up with zingers and one-liners that cracked the audience up. Poundstone even met up with then-President George Bush, despite her Democratic values.

But Poundstone couldn't escape the fact that she was filling a role that had predominantly been filled by men. The day after the dinner, the news coverage all focused on one thing: what she wore to the event itself. That's right — not her jokes, not her performance, but her outfit. As she recalled to Elle, "I think that might have been the one time that I ever thought about the fact that I was a woman. ... I just remember being struck by how much ink they wasted describing my outfit."

Conan O'Brien hosted a successful event in 1995 when he took over at the White House Correspondent's Dinner. In fact, O'Brien's night of hosting was met with praise all around, with Parade commending the comedian's ability to keep the audience entertained. One of O'Brien's most successful jokes was directed toward anyone who might be watching the night's dinner on CSPAN. O'Brien pleaded with such viewers, saying, "For God's sake, it's Saturday night! Go outside! Meet a woman! There are things you can do!" (per Parade).

O'Brien later explained to The Insider that a lot goes into planning what jokes will and won't hit at the event. As he put it, the host has to consider a lot and they have to do so with speed and skill. O'Brien said, "You've got to touch on a lot, quickly. You want it to be edgy. You want some of the oohs because you actually, you want some of it to be biting, but you also want to pull back and just have the big laughs."

Stephen Colbert is a bit of a polarizing figure in the world of comedy, as he is often outspoken about his personal beliefs and opinions. When he hosted the White House Correspondent's Dinner in 2006, his full range of comedic skills and timing were on display, and it's safe to say that not everyone enjoyed it.

Colbert took the opportunity to tear into former President George W. Bush. He took Bush to task, calling out his poll numbers and implying what was behind his 32% approval rating. Colbert joked, "We know that polls are just a collection of statistics that reflect what people are thinking in 'reality.' And reality has a well-known liberal bias." As CNN noted, people who worked for the Bush White House and some of his supporters even walked out of the dinner early after the jokes seemed to be too much. 

When Jimmy Kimmel hosted the White House Correspondent's Dinner in 2012, he seemed fairly focused on keeping the peace. As The Hollywood Reporter wrote at the time, there wasn't a point at which Kimmel lost the audience, likely owing to what seemed like his commitment to not crossing any lines. As a result, he had consistent laughs throughout the evening and was able to walk away knowing he didn't do a terrible job.

However, Kimmel did reserve a few pointed remarks for specific targets. Like Joel McHale before him, Kimmel also went after Chris Christie's size, calling out the former New Jersey governor, saying, "You might be misunderstanding the New Jersey state slogan. It's not the 'Olive' Garden State." Kimmel threw in a few jabs at Republican presidential candidate Mitt Romney as well, noting that America wasn't ready to elect a Mormon president of the United States (per The Hollywood Reporter).

When Drew Carey hosted the White House Correspondent's Dinner in 2002, he was at the top of his game as the star of "The Drew Carey Show." Carey is also a longtime advocate for the Libertarian Party, so it's not too big of a surprise that he really approached his time as host of the dinner from a more or less neutral place.

In fact, Carey largely eschewed making political jokes completely, instead deciding to go after pop culture — a meeting ground that is a little easier for everyone to swallow. One joke touched on religious holidays and their symbols, with Carey asking, "Why is the Christian religion the only one in the world that needs a mascot to sell their stuff? You don't see Jewish people out celebrating with the Passover kangaroo" (via Time). Carey's decision to avoid hot topics probably won him supporters at the time.

Michelle Wolf certainly didn't make any friends when she hosted the White House Correspondent's Dinner in 2018. In fact, Wolf herself seemed acutely aware of this fact only moments into her performance that night, when she joked that it was possible the event organizers should have researched her more thoroughly before deciding she was the person for the job (per NPR).

People who didn't enjoy Wolf's jokes that night said that they were perhaps too direct, especially the jokes about former White House Press Secretary Sarah Sanders. During one joke, Wolf likened Sanders to a character from "The Handmaid's Tale," saying, "We're graced with Sarah's presence tonight. I have to say I'm a little star-struck. I love you as Aunt Lydia in 'The Handmaid's Tale'" (via ABC News). The character in question is notoriously abusive and brutal toward other women on the show.

Things were so touchy that the White House Correspondents' Association felt compelled to issue a statement via Twitter addressing Wolf's jokes. The association noted, "Last night's program was meant to offer a unifying message about our common commitment to a vigorous and free press while honoring civility, great reporters and scholarship winners, not to divide people. Unfortunately, the entertainer's monologue was not in the spirit of that mission." But for her part, Wolf told NPR she was pleased with her jokes and happy she said what she said.

In 1996, Don Imus demonstrated that no one — not even the sitting President nor his wife — was safe at the White House Correspondent's Dinner. When the radio and TV host showed up for the night's event, he was prepared to go after former President Clinton's reputation as a bit of a lady's man (and this was still two years before the Clinton-Lewinsky scandal would erupt in Washington, D.C.). 

Imus mocked the president for the rumors surrounding himself and his relationships with women, as well as for his admitted drug use in college. Imus went on to use Hillary Clinton's legal case and then-Senator Joe Biden's reported hair transplant for jokes, and the White House Correspondent's Association ended up writing a letter to the Clintons to apologize for the night (per The New York Times).

Kenan Block, the president of the White House Correspondent's Association, told Fox News that Imus had told the organization he had no plans to make fun of the Clintons. Block explained, "He said, "I can't tell womanizing jokes about the president with his wife sitting right there,' and 'Don't worry, I'm not going to embarrass myself."

When Jon Stewart hosted the White House Correspondent's Dinner in 1997, he wasn't nearly as well known as he is today. After all, this was only months after "The Daily Show" began and Stewart hadn't yet amassed his legion of fans. In fact, he was actually the third choice as host for the White House Correspondent's Association. As Quartz revealed, the organization first asked Rosie O'Donnell and Dennis Miller to take the spot.

Luckily, Stewart did a decent job as host — even if all of his jokes didn't exactly land. Quartz describes his barbs as "a tad outdated," but notes that the jokes certainly displayed elements of the type of humor that Stewart would go on to be known and celebrated for. As Stewart asked during one joke, "Isn't that what the confirmation process is in Washington? Weeding out the truly qualified until you get the truly available?"

Many were excited when Conan O'Brien returned to host the White House Correspondent's Dinner in 2013, but he didn't really live up to his first appearance. As The Wrap put it, "O'Brien's delivery felt rushed, overly reliant on his notes and the order of his jokes and, he spoke very, very loudly."

Despite the fact that audiences at home didn't appear to love his speech, O'Brien himself walked away from the event feeling like the people in the room did. As he told The Intelligencer after the fact, to him the reaction of the people actually in attendance is all that matters. He said, "I don't read reviews, I always get the gist of it from people. The biggest reaction I get, the best, is from that room. Like, who was there and how did [those] people feel about it. That was overwhelmingly positive, so I'm very happy with that."

Elayne Boosler hosted the White House Correspondent's Dinner back in 1993 and, from everything she's said, the honor was all hers. As Boosler later told Elle, she was a huge supporter of then-President Bill Clinton, which made accepting the hosting gig an easy decision. Boosler explained, "I hosted the four-hour Constitution Hall Gala the night before the Inauguration. I met my husband at the Inauguration! I couldn't have been happier or more flattered to be asked."

However, Boosler recognized that no matter how great of a job the host of the night does, they will be torn down in newspapers and publications the next day. Boosler went so far as to tell Elle that in the end, this is just how things are done in Washington, D.C. She said that ultimately, it can be too easy for the attendees to deny, deny, deny, explaining, "Remember, it's Congress. They deny they were there. ... They're so used to covering up their affairs, cheating, and dishonesty, they can't even admit they laughed the night before."

Wanda Sykes took over hosting duties at the White House Correspondent's Dinner in 2009, and she surprised some members of the audience with her jokes and tactics. In fact, Sykes had no problem letting her personal political spill out into the open. She referred to to radio host Rush Limbaugh as a terrorist and told former vice presidential candidate Sarah Palin how to avoid getting pregnant (Palin is a mother to five children). She also admonished the audience when they booed some of her more intense jokes. As Elle notes, Sykes told the crowd, "Oh, shut up. You're gonna be telling that one tomorrow."

Others outside of the dinner were also shocked by Sykes' performance. Deadline noted that the event was the toughest one since Don Imus famously went after the Clintons. "If history is any judge," Deadline wrote, "then comedians asked to perform there seem to do best when they joke with gentle jibes rather than go for the jugular. Someone should have reminded Wanda Sykes about that before tonight."

Jay Leno has hosted the White House Correspondent's Dinner a number of times, but his 2014 performance is the one that seems to have disappointed audiences at home and in person the most. For starters, as HuffPost detailed, Leno managed to bomb the event pretty badly, and he did so using jokes that he had already performed on his late-night talk show. Ouch. 

The Wrap also reported that Leno began the night in a tough position, as Conan O'Brien had recently been dethroned as the host of "The Tonight Show" so that Leno could take over. The publication shared one of the comedian's jokes, noting that not only did it fail at the dinner, but it also failed on his show. Leno said, "If you took all the money the Republicans have spent trying to stop health care, and all the money Democrats have spent trying to get health care, we could afford health care, you know that?"