Reports that The Wanda Sykes Show will most likely not return to Fox for another season isn’t exactly a newsflash. Debuting on November 7, 2009, the Saturday-only late night show just had trouble gaining relevancy. When it comes to failing to master late night television, even when it’s a once-a-week deal, Sykes isn’t alone. Black comedians just haven’t thrived in this medium. A year earlier, D.L. Hughley failed miserably with his CNN weekly D.L. Hughley Breaks the News. To be fair, getting laughs at CNN wasn’t exactly a Las Vegas odds winner. Still, what is it about late night television that spells disaster when a little color is added to the small screen mix?

As far as the traditional daily late night show format most often associated with the legendary Johnny Carson is concerned, Arsenio Hall is the only African-American to make any significant waves. In comparison to today’s hosts, Hall had considerable training in the late night arena. A former announcer/sidekick for Robin Thicke’s dad Alan Thicke’s troubled 1984 show, Thicke of the Night, Hall got his big break filling in for FOX’s failed Johnny Carson challenger, The Late Show Starring Joan Rivers. When Rivers left in 1987 after only a year, Fox kept the concept alive by rotating in talent that included Hall and Robert Townsend. Hall’s ratings were so promising he led his own show, The Arsenio Hall Show, from January 3, 1989 to May 27, 1994.

Capitalizing on hip-hop’s mainstream emergence, Hall incorporated much of that energy into his show. Today, with The Roots serving as the in-house band for NBC’s Late Night with Jimmy Fallon as well as Jay Z, Nas, TI and many other rappers dropping into The Late Show with David Letterman, The Tonight Show with Jay Leno and several others on a regular basis, it’s easy to forget that it wasn’t always that way. For many rappers and actors of color, The Arsenio Hall Show was their first appearance in the late night format. One could argue that there’s still as much of a need for such shows but, unfortunately, the ratings don’t reflect the desire.

Hall’s success resulted in other networks gambling with black comedians in the late night talk show arena. There was The Whoopi Goldberg Show (1992-1993), The Keenen Ivory Wayans Show (1997-1998), Vibe (1997-1998) and Magic Johnson’s quickly canceled The Magic Hour (1998). BET also threw their hat into the treacherous late show ring with BET Live (1998) and BET Live from L.A. (1999-2000).

With Cedric the Entertainer initially slated to host, a BET late night show appeared promising until Cedric the Entertainer checked out suddenly amid a huge fight black comedians waged against BET for unfair labor practices. NBA champion John Salley stepped in before BET revamped the concept, re-emerging with veteran but little known comedian Michael Colyar for BET Live from L.A. Needless to say, these attempts were poor and distasteful.

As for Vibe, which Quincy Jones produced, comedian Chris Spencer just never found his way. Despite all of Goldberg’s remarkable achievements, she just failed to deliver the consistent energy late night television requires. And, Magic Johnson, well, he was just out of his element. Black comedians went to town complaining about his poor delivery and timing. Since then, however, Johnson has rebounded nicely, sticking to sports shows and guest appearances. He, however, learned the hard way: when it comes to late night, the masters make it look easy.

So far, Oscar winner Mo’Nique is holding steady with her late night talker, The Mo’Nique Show, which debuted on BET October 5 just before her amazing awards show run. Although it airs five days a week, the show, unlike Leno or Letterman, is not taped daily. It also doesn’t attempt to provide the social commentary for which these juggernauts are known. Instead, having fun is its primary goal.

Perhaps Chris Rock enjoyed the most overall success with The Chris Rock Show, where Wanda Sykes first rose to prominence. Airing on HBO from 1997 to 2000, Rock’s Emmy award-winning show had a mixture of skits, live music performances and in-studio guests. An able interviewer, Rock delivered insightful and lively conversations with such controversial figures as Al Sharpton and Allen Iverson. Although his content was largely aimed at African-American audiences, it cut across many racial lines. Rock clearly had a promising future in late night television but chose to end The Chris Rock Show in 2000 to pursue other opportunities, mainly film.

Given Wanda Sykes’ likely fate, maybe Rock has a comeback in the works. At this point, he might be the great black hope when it comes to today’s late night terrain. With hip-hop, Hall benefited from a significant cultural shift, of which Rock is a beneficiary. These times, however, clearly call for a super comedian, one prominent enough to get the time it takes to cultivate a rhythm and an audience. This late night game is harder than people think and, when it comes to black comedians, there are no Conan second chances.