Hilarious in Hindsight: On Jimmy's first night, Stephen Colbert (at the time host of Comedy Central's The Colbert Report, which aired opposite The Tonight Show) was one of the many big stars to welcome him, dumping a small barrel's worth of pennies onto Fallon's desk and shouting, "Welcome to 11:30, BITCH!" It became a bit more amusing a few months later in 2014, when it announced that Colbert himself was moving to take over David Letterman's The Late Show with David Letterman on CBS to become The Late Show with Stephen Colbert. This meant that he was still airing at 11:30, but was now competing against Fallon on one of the main broadcast networks. Even better, Jimmy Fallon made a cameo on Colbert's first night on The Late Show, bringing it full circle.
After learning that he had spectacularly bombed a blind date with Nicole Kidman (in that he didn't even realize it was one), subsequent guests have reminded him of his Epic Fail.
Tousling Donald Trump's hair has quickly become this, and may have played a part in viewers abandoning the series in favor of The Late Show with Stephen Colbert, not helped at all by the fact The Late Show eventually embraced the brand of mixing political comedy with political commentary of Stephen Colbert's previous show The Colbert Report. In a New York Times piece, Fallon himself admitted that the Trump interview was a "setback," and that he didn't do enough to address the controversy at the time.
Older Than They Think: This was not the first Tonight Show iteration that had the host and a guest sucking on helium and reveling in the hilarity of higher-pitched voices (as Jimmy did with Morgan Freeman). Johnny Carson did it with Roger Moore on his version.
So Bad, It's Good: Invoked; the premise of the "Do Not Play List" segment.
Suspiciously Similar Song: The music accompanying "Random Object Toss" sounds similar to "Sweet Georgia Brown".
They Changed It, Now It Sucks!: The game "Pictionary" used to be played the traditional way, with markers and paper, but in late 2016 Jimmy showcased a new technology that allowed you to play a virtual reality version. Fine, except the classic style is no longer played at all. It doesn't help that the drawings in the virtual reality version are sometimes harder to see, due to the contestants moving around (which, in turn, moves the picture).
Tear Jerker: Jimmy's somber, choked-up monologue in the wake of Kobe Bryant's death - especially when he recalled how the two of them met before they became famous by going on a beer run, and then promising to go on a beer run with Kobe when he saw him on the other side again.
that the Trump interview was a "setback," and that he didn't do enough to address the controversy at the time.