When you think late-night comedy, History probably isn't the first—or even the 10th—channel that comes to mind. But the network hopes to change that starting next Thursday, Feb. 25, when it rolls out a new late-night comedy block called Night Class. And it's enlisted a big name to bring the funny to History: Dan Harmon.

Harmon, the man behind Community and Adult Swim's Rick and Morty, is one of several big comic names contributing to Night Class, which will air at 11:30 p.m. Thursdays following History's new series Join or Die with Craig Ferguson. The block's collection of short-form comedic series will help History target millennial men and the advertisers trying to reach them, both on TV and online.

"When I see people talk about some of the things they're watching, it's on the fringes of the schedule, the things that really push the creative, like a late-night comedy experiment. And I realized that was new territory we could explore," said Paul Cabana, evp and head of programming for History.

Great Minds with Dan Harmon is one of three series that will debut as part of Night Class's initial lineup. (Each half hour will air programming of varying lengths, and History will begin to rotate new series in after the first eight weeks or so.) Harmon, who hosts, will sit down with comedic actors playing some of history's smartest people (including Jason Sudeikis as Thomas Edison, Kristen Schaal as Amelia Earhart and Jack Black as Ludwig van Beethoven). Great Minds will also feature Sarah Silverman, Aubrey Plaza, Nick Kroll and Dana Carvey.

As History looked for creators to contribute to Night Class, Harmon was one of the first to respond. "It turns out he is a rabid history buff, and he's like this pied piper for creatives and got all these people interested in the idea of doing a sketch about a historical figure," said Cabana. Great Minds with Dan Harmon was originally shot as a pilot for IFC last year but was completely reworked for History. Here is a clip from the Jack Black episode:

The second series, Crossroads of History, will highlight what History calls "little known but historically accurate" moments in history—like Abraham Lincoln's alcoholic bodyguard stepping out for a drink shortly before Lincoln's assassination and Hitler's failed 1908 art-school admissions interview. Actors in Crossroads include Lou Diamond Phillips, Jack McBrayer, and The Office's Brian Baumgartner and Angela Kinsey.

Night Class's third initial series, How to Lose the Presidency, shows infamous moments that helped doom presidential hopefuls—like Howard Dean's scream on the campaign trail and things that happen in the current presidential race.

History hopes Night Class will help it attract a younger audience—the network's median age is 56—and finally allow it to make some noise in the digital space. "It just made sense that we start to produce content that was as much at home on your phone as it was in your living room," Cabana said. "We're entering an age where it's about cumulative viewers and good content being forward to each other, so it's a great way for us to explore the digital space."

While Cabana said Night Class was more about reaching a new group of creatives than specifically targeting millennials, A+E Networks' ad sales team is clearly hoping it attracts younger-skewing advertisers to History.

"Our hope is this block becomes an opportunity to get into business with younger clients, maybe clients with a little more of a comedic take that don't always look to History as their first or probably second choice," said Peter Olsen, evp of ad sales for A+E Networks. "In success, we have an opportunity to talk in a much bigger way with groups of clients that we don't do a ton of business with."

Already, Olsen has seen interest from movie studios (especially those producing comedies) and video games, as well as wireless, adult beverage, automotive and other millennial-targeted brands. "When you talk to clients, they obviously want to reach that audience, but what they also want to reach is the mind-set," he said. "I don't think we're thinking this is necessarily going to be a median age of 18 years old watching this block, but younger than our normal audience … very much speaking in a millennial mind-set."

Olsen said Night Class is part of a new, companywide approach to digital experimentation. "More and more, we're talking about creating digital content short-form things but using linear as a launching pad and another place to run it," he said. "On our big brands, we're talking about doing some comedy stuff that doesn't have to be a 30-minute sitcom. It can be a five-minute comedic piece that can run on linear and on digital. So we're looking at our nonprime dayparts in a way that they can almost become digital verticals that run on linear and have a digital life as well."

It's no accident that History is rolling out Night Class a couple of months before this year's upfronts. "We're looking at this as a strategic new direction that the timing of it, just before the upfront conversation, is great for us," Olsen said. "Because when this thing pops, and it shows both a different tone as well as what we think is going to be a different audience, I think it gives us a ton of ammunition going into the upfront season."