Before he edited Deadspin.com and wrote God Save The Fan: (Longest Subtitle Ever), sports blogger Will Leitch had an online column (and later, book) called Life As A Loser. The genesis of the column was Will’s disastrous appearance on the Comedy Central game show Win Ben Stein’s Money in the Spring of ’97, the night before which young Will was unceremoniously dumped by his fiance. So co-host Jimmy Kimmel asked him about it. On the show. And then Will did what Kimmel called “The worst Woody Allen impression (he’s) ever seen.” In honor of Will’s last week at Deadspin (he’s moving on to New York Magazine), I present the most embarrassing video skeleton I’ve seen yet, which is finally, mercifully online: Will Leitch on Win Ben Stein’s Money.

Part One: “Will got unengaged last night!”:

Part Two: “We will never forget that Woody Allen impression”:

Poor Will. But eventually everyone will see their long-forgotten TV appearances on YouTube. Send ‘em here!

Comments (2)
  1. One of the things I always liked about that show was how Ben Stein would call people out for trying to get some facetime on tv (“Are you an actor?”). I never realized how common a strategy that was until then.

    More importantly, why has no one cut Jimmy Kimmel’s head off?

  2. The moment after Kimmel says “unengaged” Will’s face looks so sad! What a monster Kimmel is.

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