Democrats Aren’t the Only Ones Leaving Chicago Triumphant

How great a decision was it to choose to put on your big event in Chicago?

It sure worked out spectacularly: Huge raucous crowds, cheering, laughing, clapping for virtually every word being uttered; adoring endorsements for both the speakers and the candidate; and genuine reveling in the best that Chicago had to offer.

Oh, and the Democrats did pretty well, too.

The other big winners were the two late-night shows that decided to write a big check, decamp en masse from their homes in New York City, and relocate for a week to the heart of the Second City, which, after all, has a historic identification with great comedy.

Both The Daily Show and The Late Show with Stephen Colbert pulled off something of a throwback for late-night television when they took their shows on the road this week.

It was surely a risk. Going out of town means leaving the studio, where the comforts of regular television production are right at hand, and into much bigger digs, which are not set up for talk shows.

Late-night shows used to take trips like these routinely, to juice up ratings during sweeps weeks, and to reach out to fans in other places. They also involved considerable expense at a time when hit late-night shows had more beefy budgets because they were such reliable money-makers.

Now they’re better known for scaling back, doing things like saying goodbye to their house bands, a different sort of event which also took place this week on NBC’s Late Night with Seth Meyers, on the very same night of the Chicago finales being hosted by Colbert on CBS and Jon Stewart on Comedy Central.

What The Daily Show and Colbert proved this week was that there is certainly life left in the linear lineage of late night (and also that alliteration can be an overindulgence).

The shows generated such enthusiasm from local fans that you might be led to think that a lot of people still consume this form of entertainment. If you can fill the massive, 4,000-seat Auditorium Theater for a four-night stand, as Colbert did this week, you’ve got some serious evidence of mass appeal. That place seems to have rafters on top of its rafters, and Colbert fans packed every single rafter (even if it looked like they had to duck their heads up in the top rows to steer clear of the next rafter.)

Not for nothing, they also generated (relatively) strong ratings, despite DNC-delayed start times that pushed Colbert and his network co-horts well past midnight most nights this week.

Along the way, the shows generated inspired comedy. While their nightly monologues were generally excellent, what set the DNC-based shows apart from more standard weeks was ambitious bits, utilizing institutions of Chicago, like Wrigley Field, the oddball “Bean” sculpture, and the inside of The United Center where the convention was taking place (though not actually WHILE the convention was taking place.)

Colbert resurrected his Donny Franks character who hawked his Chicago-style hot dogs to various early-arriving Dem figures (NY Rep. AOC, Illinois Governor J.B. Pritzker, old hand James Carville) before shooting a few into the seats with a T-shirt gun. Daily Show correspondent Grace Kuhlenschmidt used the Bean as a backdrop for observations that the Democrats reproductive rights theme involved lots of references to genitals. And Colbert went as himself to Wrigley Field to interact with the locals and, of course, sing “Take Me Out to the Ballgame” at the 7th-inning stretch.

He also presented the best character sketch of the week by far in the latest visitation from Melania Trump, aka Laura Benanti, killing again with her elegantly accented impression. This time Melania lamented the fact that Kamala Harris’s husband Doug Emhoff would be the First Gentleman: “Why does she get to have a husband who’s a gentleman?”

And after an extended tantrum, featuring a dour Trump face: “She gets Doug Emhoff; I get that jag-off.”

To curry favor with the local crowd, she praised the town. “Oh, it’s vonderful. The food is so rich here I could marry it.”

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Most of the nightly themes on both shows included support for Joe Biden, Harris, and her running mate Tim Walz—which surely tested the veins in the temple of the opposing candidate, and his media backers.

But there were also legitimate shots taken at various excesses of the Democrats’ show. The Daily Show made fun of the lieutenant governors and other “who’s that?” speakers who were trotted out. On Thursday night, Stewart bounced the Democrats for promising Beyonce and delivering Elissa Slotkin.

The Daily Show host even poked holes in the pro-forma bio film that preceded Harris’s speech, which included endless praise because she occasionally uses the telephone to call people. One poor speaker who messed up and said “Harris always calls on her birthday” walked right into Stewart’s amazement that Harris called people on her own birthday to chide them for not calling earlier.

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So there was some legitimate comedy targeting of “fine people on both sides.” (Real late-night shows make the joke if it gets a laugh, no matter their political proclivities.) 

But of course Trump took the brunt of the shelling for the week. Because, well, the late-night hosts genuinely don’t love him.

They did genuinely love Chicago though, and Chicago loved them.

For just about everything but choice of pizza.

They can get a slice when they get back to town, a celebratory slice for an outstanding week’s work.

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