Craig Kilborn seemed to have disappeared from broadcasting but then surprised people by returning with "The Kilborn File." Fox decided to try this program for a six week summer 2010 run in the 7-8pm time slot (for a handful of the big market affiliates that ran it), as a kind of extended pilot to see if it might play on the full network, but it was really just Kilborn's version of the CBS Late Late Show he hosted years prior, cut down to a half hour.
All of the elements were there: the wry, know-it-all manner in his monologue, the news stories from his desk (with the addition of Christine Lakin, his "Huckleberry Friend" and apparent sidekick). There was time for one guest to interview (including his famed "Five Questions"), and the games he played, which had to be renamed and ever so slightly altered to avoid some intellectual property lawsuits, I presume.
The reason "The Kilborn File" didn't work is very simple: it was a cheap copy of the original in a world where people like Craig Ferguson, Conan O'Brien, George Lopez, Jimmy Kimmel... and even Jimmy Fallon had moved the talk show genre to new, different and interesting places. This just felt like they were trying to figure out how to do Kilborn's Late Late Show all over again but in a thirty minute format. I suppose the producers of this program didn't know you really can't recreate the same show, years later, unless it's a lot better than the original. This was, at best, half as good.
There is also a question about whether viewers wanted to see a talk show at the hour it aired, between the daytime talk of The View, Oprah, Ellen and the rest that aired in 2010 and those late night programs that this aspired to be, Kilborn may have been a partial victim of "Jay Leno Misplaced Talker Syndrome." But I suspect that if the show had been more innovative, more entertaining and more amusing, people might have sought it out.