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20 Years Since Dennis Miller and the Best Monday Night Football Season Ever

Sean O'Leary
7 min readSep 28, 2020

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ESPN has been trying to recreate the magic of the 2000 Monday Night Football season for 20 years now. They’ll never succeed.

Monday Night Football was the premier sports series in the country entering the 21st century, and there wasn’t a close second. College football wasn’t in primetime every weekend. The NHL was barely on television. Baseball was still struggling after the 1994 strike. The NBA lost Jordan and endured a lockout season that tanked ratings.

Despite being such a highly-rated show, Monday Night Football was going through an existential crisis in 2000 because it wasn’t the power it was in the 70’s or 80’s. So ABC swung for the fences and hired Dennis Miller as a color analyst.

Today, Dennis Miller is another washed-up celebrity throwing away his career by supporting Donald Trump. In 2000, he was one of the country’s most well-known comics. He had no background in sports. It was the most head-scratching hire in sports history.

Yet that entire summer, it was all anyone could talk about. I was beginning my sophomore year at George Washington University in the fall of 2000, and it’s all we could talk about too. We always got together weekly to drink, smoke, and watch Monday Night Football. That first game, though, felt like Christmas arriving. What would happen?

What happened is the single greatest season of Monday Night Football ever, and it had very little to do with…

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