[[folder:Steve Allen (1953-57)]]
* On the first show, Steve opened with "This show is going to go on forever." He was referring to the show's length (at the time) of an hour and forty minutes, but many TV people like to joke that Allen was psychic.

[[folder:Jack Paar (1957-62)]]
* Jack [[RageQuit quit on-air during an episode]] because [[ExecutiveMeddling NBC disliked a joke he made]] using the abbreviation "WC", which can stand for "Water Closet" (bathroom) or "Wayside Chapel", to the point of airing a news report over said joke. Before leaving, [[JerkSue Jack]] said "I am leaving ''The Tonight Show''. There must be a better way of, uh, making a living than this." His announcer Hugh Downs was forced to finish the show himself.
* A month later, Jack returned with the explanation "As I was saying before I was interrupted... When I walked off, I said there must be a better way of making a living. Well, I've looked... and there isn't."

[[folder:Johnny Carson (1962-92)]]
* 1973: Johnny had invited Uri Gellar on the show to demonstrate his "psychic spoon-bending" abilities he was promoting at the time. Carson, a former magician, suspected (rightly) that Gellar was making use of simple stage tricks, and with help from James "The Amazing" Randi set up a test which showed Gellar unable to bend ''a single spoon'' in front of the camera.
* Early 1970s: During a period where the show was still doing live commercials, announcer Ed [=McMahon=] was doing one for Alpo dog food which involved him sitting in a chair, pitching the product while feeding a small dog on the floor...but the dog wasn't hungry and wandered away. The camera went to a tight shot on Ed's face for an instant before pulling back to show that Johnny had come on-set on all fours, barking and (pretending to be?) eating the dog food himself!
* When Michael Landon was a guest star in one early '80s episode, he complained about the National Enquirer and how they make up sensational celeb stories to sell copies. He told the audience that the $2 it would cost to buy a copy of the Enquirer could go to so many better causes, and asked them to not support them. ''It received roaring applause.''
* He had on Frank Zappa in the middle of uproar over the PMRC hearings and had a very intelligent, eloquent discussion about censorship. To see the biggest talk show host in America (maybe all time) take such a stand in defense of the First Amendment is truly inspiring.

[[folder:Jay Leno (1992-2009/2010-2014)]]
* In one episode, Jay had on various talent acts. One of them was Anastasia, a dog whose owner said she could pop 60 balloons in 30 seconds. [[https://www.youtube.com/watch?v=lNnr7Grj1Eo The dog passed in flying colors.]]
* May 29, 2009: On his last show before a small hiatus, Leno revealed all the kids who were born to crew members during the show's run. "And that's what I would like my legacy to be: when these kids grow up and say "Hey mom, dad, where did you guys meet?", I want them to say "We met on the set of ''Series/TheTonightShow''"."

[[folder:Conan O'Brien (2009-10)]]
* June 1, 2009: As strange as it might be for what's effectively a series premiere to have an MOA, Conan's first show began with the NBC "In Living Color" Peacock and voiceover followed by a sketch of Conan sitting in his New York apartment, going over everything he needed to do to prepare for the show, and realizing he forgot to ''move to Los Angeles''. Unable to hail a cab, he proceeded to ''sprint across the entire nation in a single morning'', while [[CrowningMusicOfAwesome "Surrender" by Cheap Trick]] played in the background.
** And when he got there, he realized he left the studio keys in New York...so he ''drove through the wall with a bulldozer''.
** The song of choice and its artist is a FunnyAneurysmMoment, considering what NBC pulled later on.
* January 12, 2010: [[http://www.dailynews.com/news/ci_14173746 Conan's open letter refusing to host ''The Tonight Show'' if they moved it to 12:05 AM to accommodate Jay Leno.]]
** Could also qualify as a FunnyMoment (he concluded the letter by apologizing for his hair) and a HeartwarmingMoment (as he was unwilling to damage the legacy of either ''Series/TheTonightShow'' or ''Series/LateNight'' by taking the later timeslot).
* January 20-22, 2010: With his time on the show running out, Conan announced that he'd be exploiting a loophole in his contract to do whatever he wants on NBC's dime.
** January 20: Blowing $1,500,000 dressing up the world's most expensive car as a mouse and playing the original master recording of The Rolling Stones' "Satisfaction".
** January 21: Followed up by buying a Jockey and a 2009 Kentucky Derby winning race horse wearing a mink Snuggie watching restricted NFL footage. Total cost: $4,800,000.
** January 22: On his final episode, he bought an original fossil of a Giant Ground Sloth from the Smithsonian, which was spraying beluga caviar on an original Picasso painting. Total Cost: '''$65,000,000!''' Too bad Conan had to admit it's not real...
*** Although all of the products he displayed during his "New ''Tonight Show'' Mascot" segments were rented or on loan from other organizations, the music ''certainly wasn't''. According to comments made by Roots drummer Questlove (on his Twitter page), many of the tracks Conan used during his final week were on ''NBC's banned/restricted music list'' because the rights to clear them were '''through the roof'''. For instance, the music that played when Tom Hanks appeared on Conan's finale (the Beatles' "Lovely Rita", in tribute to Hanks' wife) costs '''$500,000''' in clearance rights. Yes, Conan really did stick it to NBC in his final week. ''And it was awesome.''
* January 21, 2010: Pee-Wee Herman's explanation of the late-night debacle. Although beginning normally, with an ''adorable'' stuffed giraffe ("That's you, Conan") and NBC Peacock, it escalated into the most awesome thing ever Conan's attorney, according to Pee-Wee, is '''''[[{{Transformers}} OPTIMUS PRIME.]]'''''
* January 22, 2010: Conan's final speech. All throughout the week, he had made several escalating jabs at NBC management, and everyone expected him to end his tenure with some snarky commentary on the way the show was handled. Instead, he ended with this ''after thanking NBC'':
-->"I hate cynicism. For the record, it's my least favorite quality. It doesn't lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you're kind, amazing things will happen. I'm telling you. Amazing things will happen."
* January 22, 2010: The very last moments of Conan's tenure himself (on guitar), Will Ferrell, Billy Gibbons (of ZZ Top), Beck, Ben Harper, and the ''Tonight Show'' Band playing a rendition of "Freebird" in front of a giant American flag. Ferrell even played the [[Series/SaturdayNightLive cowbell]] at one point. It was more awesome than [[MemeticMutation the goddamn Batman]].

[[folder:Jimmy Fallon (2014-)]]
* February 17, 2014: On his first night, he allowed Joan Rivers to appear after Johnny Carson (and out of respect for Carson, Jay Leno) banned her for a quarter of a century because of a grudge.
* March 21, 2014: Jimmy decided to decree that dancing was illegal on the Tonight Show. His guest was Kevin Bacon. Mr. Bacon was not amused. As such, he decided to express his displeasure in a very [[{{Film/Footloose}} familiar]] [[https://www.youtube.com/watch?v=3T2FpCDlyNg style]].
* After a lip sync battle with EmmaStone, Jimmy declared Stone was the winner hands down after her incredible [[https://www.youtube.com/watch?v=bLBSoC_2IY8 lip sync performances of "Hook" by Blues Traveler and "All I do is Win" by DJ Khaled]].
* Will Ferrell and Chad Smith's epic drum-off, culminating in [[https://www.youtube.com/watch?v=0uBOtQOO70Y a surprise performance of "Don't Fear the Reaper" by the Red Hot Chili Peppers]].
* You ''will'' believe that [[Creator/DanielRadcliffe Harry Potter]] [[https://www.youtube.com/watch?v=aKdV5FvXLuI can rap]].
* February 1, 2015, the post[=-=]UsefulNotes/SuperBowl XLIX live show: Jimmy took the show to a commercial break, but announcer Steve Higgins suggested that the program should "go out big." After Higgins pulled a lever, the curtains were drawn, and Creator/ArnoldSchwarzenegger (as the Franchise/{{Terminator}}) [[https://www.youtube.com/watch?v=FG2f0pKr2JY appears to thunderous applause from the audience]], and later declares, "[[CatchPhrase We'll be back!]]"
* February 4, 2015: Jimmy took the show back to LA for the first time since he took over. He then realized a dream dating back to his first year of Late Night, as for the first time since 1994, the cast of Series/SavedByTheBell (minus Lark Vorhees and Dustin Diamond) reunited. Not just that, but in character, and with a spot on recreation of the iconic Bayside High hallway. Bonus points for references to the cast's post-SBTB careers, complete with Elizabeth Berkley's DeathGlare at referring to Jessie [[{{Film/Showgirls}} becoming a stripper]], and Mario Lopez not aging one damn bit.
** Jessie's character was an outspoken feminist, meaning that reaction totally fit the character!
* On September 23, 2015, Jimmy surprised and overjoyed many a 90s kid with a ''completely new [[Series/AllThat Good Burger sketch]]'', [[https://www.youtube.com/watch?t=4&v=odQQ4jgGpFU bringing back both Kenan Thompson and Kel Mitchell]] for their respective roles, and faithfully replicating the original Good Burger restaurant set.
* ''Wrestling/TheUndertaker'' shows up out of nowhere - complete with his trademark BigEntrance - just to [[https://www.youtube.com/watch?v=MFiRImul_d0 give a Tombstone]] to a guy in a turkey costume.[[note]]And not just any guy - it's Wrestling/{{WWE}} also-ran Brad Maddox![[/note]]
* February 5, 2016: Jimmy's "Puppy Predictors" were summoned to [[https://www.youtube.com/watch?v=QU66JJHIT7w predict the outcome]] of UsefulNotes/SuperBowl 50. Jimmy placed two food bowls with Denver Broncos and Carolina Panthers insignia, respectively. When the puppies were released, the majority of the puppies headed to the Broncos food bowl, and the Broncos were declared the winners of Super Bowl 50. Two days later, in the actual Super Bowl 50, the Broncos '''actually defeated''' the Panthers 24-10! Coincidence? Doubtful.
* [[https://www.youtube.com/watch?v=7TJ7IUNWGl4 December 7, 2016]] saw an appearance by [[Creator/{{Nintendo}} Nintendo of America]] president Reggie Fils-Amie, who let Jimmy demo ''VideoGame/SuperMarioRun'' live with Creator/ShigeruMiyamoto himself cheering him on in the audience. After that, Reggie managed to surprise both Jimmy and fellow Nintendo fans by doing a surprise live demonstration of ''VideoGame/TheLegendOfZeldaBreathOfTheWild'' '''on the UsefulNotes/NintendoSwitch!'''[[note]]For those out of the loop, Nintendo gave out hardly any information about the Switch in the months leading up to its October preview trailer, and publicly stated that they would not provide any more info about the console until January 2017[[/note]] You could just ''tell'' how overjoyed Jimmy was to be able to experience all this in one night.