Republican presidential candidate contest: Jeb Bush set to get a roasting on The Late Show with Stephen Colbert

It was perhaps the crowning moment of Stephen Colbert’s career so far. In 2006, at the annual White House Correspondents’ Dinner, he delivered a merciless comedic roasting of George W Bush, while the then-President sat powerless and unamused just two chairs to his right.

On 8 September, Colbert will get to toy with another Bush, when Dubya’s brother, Jeb, appears as a guest on the premiere of The Late Show with Stephen Colbert. The former Florida Governor is running for the White House; Mr Colbert is taking over the slot in the CBS network’s late night schedule occupied for the past 22 years by David Letterman. It’s hard to say which man ought to be more nervous.

In Colbert’s previous job, as the host of Comedy Central’s The Colbert Report, he played the role of “Stephen Colbert”, a bloviating conservative political pundit, equal parts self-regard and stupidity. By all accounts, the entertainer will shed that persona for The Late Show, but with the 2016 US presidential race crying out for comic treatment, he could hardly leave the political arena behind. Besides Mr Bush, The Late Show’s line-up for September includes Vice-President Joe Biden, the Democrat presidential candidate Bernie Sanders and the UN Secretary-General, Ban Ki-moon.

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Actors such as George Clooney and Scarlett Johansson will also appear during the show’s first week, but the movie stars who tend to populate US late-night television will be joined, on Colbert’s show, by an eclectic mix of musicians, business leaders, writers and intellectuals, among them the Uber chief executive Travis Kalanick, rapper Kendrick Lamar, and author Stephen King.

“You can’t live by celebrities alone, and they often make the least interesting guests,” said Brian Lowry, Variety’s television critic. “Some of the best interviews on The Colbert Report were with authors and people from other spheres. He’s still going to have to book his share of Bradley Cooper types, but it’s smart to try to make the show more of a salon of ideas. Colbert is an extremely thoughtful, well-rounded guy who can talk about a variety of subjects in an intelligent way.”

Colbert, 51, was brought up as an observant Catholic in South Carolina, the youngest of 11 children. When he was 10, his father and two closest brothers were killed in a plane crash. He credits his mother Lorna’s example for his sanguine attitude to that tragedy, and to life in general. Speaking to Judd Apatow for the film-maker’s recent book Sick in the Head, a collection of interviews with comedians, Colbert said: “My mom was not bitter. She did not become a bitter person. She had an excuse to be, and she did not. She stayed grateful for life.”

After studying theatre at Northwestern University in Chicago, with the intention of becoming a serious dramatic actor, Colbert was then drawn into the city’s improvisational comedy scene, becoming a regular cast member at the celebrated Second City comedy improv theatre.

Andrew Alexander, the longstanding chief executive of Second City, said Colbert fulfilled all the requirements of an improv performer – he was intelligent, well-read, a generous ensemble player, “and, obviously, he was very funny”. He added: “What you get at Second City, which is hard to find elsewhere in the comedy world, is that you do eight shows a week for maybe two to three years, and that means you just become very, very good.”

At Second City, Colbert performed alongside several future comedy luminaries including Steve Carell, who was later a fellow cast member on The Daily Show, which Colbert joined as a correspondent in 1997. His success as a foil for that show’s host, Jon Stewart, earned him a hosting gig of his own, and The Colbert Report debuted in 2005.

The “Stephen Colbert” character was the archetypal patriarchal white man; and when Colbert was unveiled as Letterman’s Late Show replacement, many wondered why CBS had picked him over a woman or a non-white host. CBS president Les Moonves told The New York Times: “I know people were clamouring, ‘Well, why don’t they get a woman? Why don’t they get somebody diverse?’ All of which we considered.” But when Colbert emerged as a candidate, Mr Moonves said, “there’s not anything better than that”.

The network and its new star have engaged in a publicity blitz leading up to the launch of the revamped Late Show, with Colbert giving lengthy interviews to GQ and Time, appearing in several comic YouTube clips, hosting a podcast and even becoming the new voice of the smartphone traffic app Waze.

While he may have to soften some of his schtick to appeal to a wider, middle-American audience, it is plain that he has lost none of his fearlessness and bite.

This week, Mr Bush sent an email to supporters inviting them to donate $3 to his election campaign in exchange for the chance of winning a ticket to his Late Show appearance. The problem? He did not consult Colbert first. So, Colbert made a video announcing a rival ticket contest, for which entrants must donate $1 to a veterans’ charity. “Where’s my cut of that sweet three bucks, Governor?” he asked. Before he even takes a bow, Colbert has his first guest on the back foot.