At the top of my list of awkward film/TV moments is this scene from Swingers, in which Jon Favreau's character fills up the answering machine of a lovely lady whose digits he'd only received that evening.
But that's fiction. The new #1 is reality. Apparently reading sports highlights is far more difficult than one would imagine. Force yourself to watch the entire clip, as the response from the anchors when they go to commercial break is priceless.
I was reminded of this clip on Doug Richards' Live Apartment Fire blog. A long-time Atlanta TV reporter, Richards excels at sharing his insightful and humorous perspective of local news.