When David Letterman left NBC for CBS, he engaged in some public bickering with his old bosses over what would remain the “intellectual property” of the network, which left some wondering whether he was going to be allowed to bring some of his most popular Late Night bits to his new Late Show. The kerfuffle proved to be no big deal, as Letterman and his writers just renamed the segments and proceeded as normal. Because, what… They weren’t going to keep doing a nightly Top Ten List?

The Top Ten List debuted on Late Night With David Letterman on September 18, 1985, and quickly became a staple, because the format was so flexible, repeatable, and sharable. The list could be completely absurd, or ripped from the day’s headlines. It could be read by Letterman or by a series of guests, accompanied by pictures and video or just by words on a screen. Most importantly, because the jokes were short and the segment ran every night, the best pieces could re-run on morning TV and radio shows.

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These 10 Top Tens are all drawn from the four book collections that were released in the 1990s: two from the NBC era (published by Pocket Books), and two from CBS (published by Bantam). Together they illustrate how the feature developed, and double as a mini-history of American culture from 1985 to 1996—including the history of Letterman himself.

10. Top Ten Words That Almost Rhyme With “Peas”

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For the record, here’s the complete contents of the first-ever Top Ten List: Heats, Rice, Moss, Ties, Needs, Lens, Ice, Nurse, Leaks, and Meats. It was typical of Late Night circa 1985 to introduce something with a lot of buildup, and then have it be puny and ridiculous. Since the show’s writers have said that the Top Ten was inspired by the breathlessly excited, self-important listicles dominating magazine covers and newspaper sections, their first list was—to borrow from the parlance of our times—perfect. Plus it gets bonus points for containing “meat,” one of Letterman’s go-to comedy words.

9. Top Ten Body Parts Or Van Pattens

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Sometimes the art of a gag involves taking advantage of the audience’s dawning awareness. Most Late Night viewers would’ve realized in about five seconds that this list was headed straight for a “Dick” joke, but Letterman makes them wait through a straight-faced rundown anyway, alternating between “kidney,” “Vincent,” “trachea,” and “Joyce” before getting down to business. This list also speaks to the Late Night writers’ understanding of how much Letterman likes names and words that sound kind of smutty. (See also: Buttafuoco, Joey.)

8. Top Ten Courses For Athletes At SMU

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Reading back through 20-year-old Top Ten lists, what’s remarkable is how many of them could be repeated today almost verbatim, with only a few names changed. This one was a reference to the then-shocking revelations about recruiting and academic violations in the Southern Methodist University football program, which would eventually lead to the school being hit with the NCAA “death penalty,” banning the team from competing for a year. Not only has there been a fresh one of these scandals every few years since, but the Late Night writers’ fake classes here (“Subtraction: Addition’s Tricky Pal,” “The First 30 Pages Of A Tale Of Two Cities: Foundation Of A Classic,” “The Denny’s Menu: Recent Discoveries,” etc.) would still get a laugh now. And while Letterman might need a new actress to sub into the “From First Love to Looker: The Films In Which Susan Dey Appears Naked” entry, the principal of that joke remains sound.

7. Top Ten Ways The World Would Be Different If Everyone Was Named Phil

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Even back in his stand-up days, Letterman’s comedy was rooted in the juxtaposition of the inflated and the ordinary. That’s why he had so much fun doing the “Small Town News” segment on his show, enjoying how the seriousness of print journalism could become preposterous when applied to craft fairs and petty crimes. There’s nothing especially brilliant about the idea of this list, beyond Letterman’s usual amusement at taking a normal, everyday name like “Phil” and imagining it as the most important in the universe. But the writers get a lot out of the premise, coming up with entries like, “Almost impossible to get the personal license plate ‘Phil,’” (it’s the almost that sells that joke), and “007 fans look forward to classic line, ‘Bond. Phil Bond.’”

6. Top Ten Ways NBC News Can Save Money

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Letterman never shied away from biting the hands that were feeding him at either of his home networks. When NBC started fading in the ratings at the end of the 1980s, he openly ridiculed the decisions being made by upper management, including in this list ripping the cutbacks in the venerable NBC News department. Letterman takes shots here at the net’s corporate parent (“Stop buying G.E. bulbs and get some that don’t burn out so fast”) and programming priorities (“Somehow incorporate news items into The Cosby Show”). He also reads off two ideas that seem strangely prescient: “Make stuff up,” and “Every night have Brokaw turn on portable TV and say, ‘Shall we watch the CBS news together?’”

5. Top Ten Good Things About Having Madonna On Your Talk Show

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For a couple of years after Letterman moved from NBC to CBS (and from a 12:30 a.m. start time to 11:30 p.m.), he was hosting not only the most popular talk show in late night, but also a program where watercooler moments seemed to happen every couple of weeks. This list was inspired by a Madonna appearance which saw the singer verbally sparring with the host and swearing like a sailor. Always a shrewd self-mythologizer, Letterman would keep referring back to that interview, as in entries here like, “For the first time, you understand why Sean Penn went nuts,” and “The host can sit back, relax, and let the censors do all the work.”

4. Top Ten Rejected James Bond Gadgets

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In the Late Show years, Letterman’s Top Tens have often leaned too heavily on topical references and name-dropping, but aside from, “Telephone filter that makes caller’s voice sound like Harvey Fierstein,” this list is more a classic inventory of things the host finds funny, from junk food (“Glove compartment Slurpee machine”) to dick jokes (“Special implants that turn 007 into a 009, if you know what I mean”) to advertising copy (“Underground laboratory that will have your glasses ready for you in about an hour”) to office supplies (“Stapler with hidden Scotch tape dispenser”) to pants (“Ejector pants”). The funniest entry though is “Pepper grinder that dispenses a little too much pepper,” which is like a leftover from the Late Night days, when Letterman could wring humor out of the mildly weird.

3. Top Ten Rejected Disney Movies

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Here, on the other hand, is a Late Show list that’s almost all jokes that are dated now: “101 Snoop Doggy Doggs,” “The Parent Trap ’96 starring Lyle and Erik Menendez,” “Huey, Dewey, and Limbaugh,” and the inevitable “Swiss Family Buttafuoco.” Top Tens like these aren’t as funny as they once were, but they serve as a valuable document of what was dominating the cultural conversation in the not-so-distant past.

2. Top Ten Other O.J. Defense Rhymes

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Nothing was as talked-about on late-night television in the mid-’j90s as the O.J. Simpson trial, and while Late Show didn’t obsess over the Simpson case the way that Jay Leno’s L.A.-based Tonight Show did (with its nightly parade of “Dancing Itos”), Letterman was always willing to approve an O.J. bit if it was funny. What makes this list work is the obvious thought put into rhymes like “If you think about Fuhrman, it’ll / Make you vote for an acquitt’l,” and, “The Bronco’s idling right outside / So acquit the man and let him ride.” The list is both silly and satirical, pulling apart the appallingly effective theatrics of the Simpson defense team.

1. Generic Top Ten List

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Even Letterman’s writers recognized their tendency to go to the same wells far too often to fill out a Top Ten, but as with the Disney movies list, this “generic” batch is most useful for now for how specific it is. Want to journey back to 1996? Read a list that features “Dr. Kevorkian’s Suicide McNuggets,” “Just two more marriages and Liz Taylor wins a mountain bike,” and, simply, “Quayle.” This was the genius of the whole Top Ten list concept, that it could contain both Letterman’s comic sensibility and whatever the writers happened to be talking about that day.