Top 10 Stephen Colbert Moments

While he likely didn’t feel lucky at first, Colbert managed to turn a decision by Comedy Central’s corporate parent Viacom to cancel an appearance by Daft Punk on The Colbert Report into comedy gold. After explaining how he’d only just found out the day before that another Viacom subsidiary MTV had exclusive performance rights to the French duo, he started dancing to Daft Punk’s hit Get Lucky. Various celebrities joined him in an original music video, most notably Breaking Bad star Bryan Cranston on rollerskates in what looked like a disco. When life gives you lemons, you make a funny video.

Stephen Colbert can host anything well. He proved it when, during the break between the Colbert Report and The Late Show, he took over hosting duties for one episode of a local Monroe, Michigan public access show “Only in Monroe”. He interviewed the show’s regular hosts and brought up a very local and impressively out of date Yelp review before introducing his special guest, Michigan native Eminem, whom Colbert referred to by his given name Marshall Mathers. After pretending not to know his guest was famous, the pair co-presented the ultimate local show segment, a real Monroe, Michigan Community Calendar.

Colbert’s political comedy can be witty highbrow satire, but sometimes downright crude and juvenile gets the point across just as well, if not better, as Colbert demonstrated when lampooning Donald Trump and his administration. Colbert has used drawings to explain everything from the Access Hollywood tape scandal to Republican Devin Nunes' conflict of interest. While the audience in the Ed Sullivan Theatre gets to see the whole work, at some point CBS will often blur out part of the image, prompting Colbert to playfully speculate as to just when that will happen.

Colbert has made a career out of parodying conservative pundits, but it turns out the host is willing to take it to the next level, imitating over-the-top conspiracy theorists like InfoWars host Alex Jones - which he does on the Late Show as Tuck Buckford. Colbert nails Jones’ mannerisms, his style of speaking, or rather shouting, and his far-out theories which, let’s be honest, don’t need to be exaggerated that much to play as comedy. The parody certainly made an impression, as the real Alex Jones brought up Colbert in his custody battle with his wife. Naturally, this shoutout only served as more fodder for the comedian.

Colbert’s 2016 Presidential Election coverage started as over-the-top humor, but ended on a very serious note. During the primaries, it was presented as the “Hungry for Power Games”, with Colbert in full Caesar Flickerman-inspired garb, giving a send-off to candidates who left the race as though they were fallen tributes. He also brought this character to both conventions, notably storming the stage at the RNC. Then, on election night, he hosted a live special called “Stephen Colbert's Live Election Night: Democracy's Series Finale - Who's Going to Clean Up This ****?” that very quickly turned from a comedy show into one of shock and reflection as the results poured in. Nonetheless… it was quality programming from beginning to end.

It’s clear that one of the inspirations for Colbert’s over-the-top conservative character on The Colbert Report was the bombastic now-former FOX News host Bill O’Reilly. In character, Colbert called him Papa Bear and when the two met in person on each other’s respective shows, Colbert’s mocking adoration was palpable. He promoted O’Reilly’s book on his show with a 30 percent off sticker and allegedly stole the microwave from the break room when he was a guest of the FOX host. When O’Reilly was fired, Colbert responded both in his old character and as himself, finally getting to say what he really thought of Papa Bear.

Colbert’s over-the-top character was at its best when paired with former Daily Show host Jon Stewart playing the straight man. This dynamic reached its peak when the pair co-presented at the 2006 Emmy Awards, in what was arguably one of the most memorable Emmy bits in the show’s history. As Stewart read a prepared script on reality shows from the prompter, Colbert, fully in character, laced into the assembled crowd of Hollywood celebrities calling them Godless sodomites praying to a golden idol, the Emmy statue. After the crescendo, Colbert jokingly admitted that it all had to do with his losing an award that evening to Barry Manilow. Classic Colbert.

Stephen Colbert is no stranger to controversy or mocking the administration. The two combined when the host decided to go after President Trump for his treatment of CBS journalist John Dickerson. The epic Late Show monologue rant that ensued culminated in a crude joke about Trump and Putin, which some initially characterized as homophobic. Colbert later apologized for his choice of words but not for slamming Trump. With an army of Trump supporters criticising Colbert and eventually the President himself making a comment, Colbert was clearly satisfied with the controversy this bit caused.

In 2006, the White House Correspondents’ Association gave Colbert a chance to perform his faux-right wing George W. Bush-praising character for the man himself when they invited him to host their annual dinner. The Colbert Report host did not disappoint and most certainly did not hold back. He went after everything from Vice President Dick Cheney accidentally shooting a man in the face to the Bush administration’s failing poll numbers and the President’s track record of standing on aircraft carriers and “rubble” alike. Colbert even took part in a skit with the legendary White House correspondent Helen Thomas. Bush’s face throughout said it all - the man was hitting his mark.

Before we unveil our top pick, here are a few honorable mentions:
- On-Air Eulogy for his Mother

“The Colbert Report” (2005-14)



- The Word: Truthiness

“The Colbert Report” (2005-14)



- Friday Cover

“Late Night with Jimmy Fallon” (2009-14)

Some satirists tell jokes to highlight the problem of money in politics, but Colbert took things to an almost surreal level by starting his own political Super PAC capable of accepting large, anonymous donations for REAL. This gave him over a year’s worth of recurring material for his show, and quite a bit of information on the political funding process for his audience. He raised nearly $774,000, much of it from not so anonymous donors whose names rolled across the screen as heroes. In the end, on behalf of Ham Rove, his lunchmeat strategist, he donated the money to the Hurricane Sandy Relief Fund and groups fighting for campaign finance reform, among others.