The notes are sarcastic in tone and involve current events, people in the news, or things that annoy Jimmy (e.g. "Thank you, pony tails, for turning the backs of girls' heads into horses' butts").
However, Jimmy discovers that the first place prize money for glee club sectionals (a flyer for which is conveniently posted in the hallway outside Studio 6B across from a row of lockers) is $380, so he decides to gather the Late Night crew – including A. D. Miles, Paula Pell, Bashir Salahuddin, and Abby Elliott from SNL – together to compete.
Jimmy has performed original songs such as "I'm Gettin' Drunk on Christmas", "I'm Goin' Huntin' for Cougars", one about the Deepwater Horizon oil spill called "[Tar] Balls in Your Mouth" (which Jimmy later revealed on the October 31, 2011 episode of Conan was his first choice for the name of his Ben & Jerry's ice cream flavor "Late Night Snack"), "The Ballad of Steven Slater", "Gonna Eat That Talkin' Sandwich: The Sarah Palin Song", "The Ballad of Anthony Weiner" (which repeatedly used the term "sucks, Weiner"), and "Walk of Shame" (accompanied by Dave Matthews).
While Jimmy is singing, often some people wearing yellow tracksuits and sunglasses (usually including Seth Herzog and Mike Dicenzo, one of them without pants), as well as the Product Placement Preacher start dancing behind him.
After a cloud of smoke obscures the camera, Jimmy, the Roots, and some of the show's African-American writers (including Bashir Salahuddin) don dashikis and sing about snack foods (such as Hot Pockets or Ben & Jerry's) in the style of African choral group Ladysmith Black Mambazo.
In a recent version, Chris Kattan appeared as a depressed skateboarding teenager who reviews monster truck shows; when the hosts got him to open up about what was bothering him (beliefs he is unloved by his father), they cut him off and finished the sketch.
He will begin by talking about his own life (his appearance on CSI: Crime Scene Investigation, his new position as host of Punk'd), but then start rambling on about more serious topics, such as John F. Kennedy assassination conspiracy theories, the subprime mortgage crisis, his fears that China's economy will overtake that of the United States, and the ethics of human cloning.
In each instance of the sketch, a different set of bizarre complications ensue, involving Jimmy in outlandish situations (such as the accidental death of a co-worker and their attempts to hide the body because the graphic artist is on parole didn't want to go back to prison for her murder; although at the end she was only unconscious) which push the actual "Head Swap" to a secondary issue.
Jimmy reviews several terrible (real) books (such as How to Avoid Huge Ships: Second Edition, Castration: The Advantages and the Disadvantages, Cooking With [Winnie the] Pooh, and Knitting With Dog Hair) and suggests people not read them.
He then brings out Kump for an interview, which shows off some of the comical mispronunciations, improper enunciation and misuse of punctuation (i.e. saying the word "slash" when a "/" appears in the script) that are prominent of computer-generated voices.
[35] Jimmy claims Facebook started their own newspaper and reads headlines from it, which are usually about the people on it (e.g. "Lonely Stay-at-Home Mom Won't Stop Posting About How Hot Adam Levine Is".
"[47] Although usually done solo at his desk, Jimmy has occasionally teamed with a guest on the segment (e.g. Steve Carell in June 2022) as they sit in rocking chairs on a set resembling a rustic country porch.
Jimmy challenges three audience members to a karaoke contest where they sing quotes from a celebrity, including Nicole Polizzi, John Madden and Mel Gibson; most installments use quotes from American conservative politicians and commentators, including South Carolina governor Mark Sanford; Tea Party convention speakers Tom Tancredo, Joseph Farah, and Sarah Palin; Fox News hosts Glenn Beck and Sean Hannity; and, most frequently, Rush Limbaugh.
(An installment of the game after the House vote on the 2010 health care legislation featured Rep. Henry Waxman (D-CA); the Congressman's face had a smaller-than-usual mouth hole but added cutouts for his nostrils.)
On the June 15, 2011 show, Jimmy hosted the finalists in Rolling Stone and Garnier Fructis' "Choose the Cover" contest (Lelia Broussard from Los Angeles, California, and The Sheepdogs from Saskatoon, Saskatchewan).
Similar to Battle of the Instant Bands, Jimmy selects three singer/songwriters from the audience and has them write a short song based on a different nonsensical phrase like "turtle sunrise" or "clouds are people too".
Johnston (played by Bobby Tisdale) is a stereotypical redneck, dressed in a pair of overalls, a trucker's hat, and no shirt, in addition to a huge mouthful of chewing tobacco and an exaggerated Southern accent.
Jimmy gave the new president a "presidential starter kit", including a copy of the Late Night by-laws, a quill pen, a carton of cigarettes, a stapler, and a first lady with "shapely arms".
Segments have included two men as Angelina Jolie and Jennifer Aniston, two white women as 50 Cent and Rick Ross, Perez Hilton and Carrie Prejean, Adam Lambert and Clay Aiken, and Glenn Beck and Keith Olbermann.
Notable celebrities joined include Hugh Jackman, Ellen DeGeneres, Steve Harvey, Jane Fonda and Lily Tomlin (as the cast of Grace and Frankie and, most lately, Keke Palmer.
California Dreams cast members Brent Gore (Matt Garrison), William James Jones (Tony Wicks), Heidi Noelle Lenhart (Jenny Garrison), Kelly Packard (Tiffani Smith), Jay Anthony Franke (Anthony Sommers), Jennie Kwan (Sam Wu), and Michael Cade (Sly Winkle) briefly discussed what they're doing now: Gore is working with a non-profit in Los Angeles, Jones is attending Pepperdine University in pursuit of a master's degree in clinical psychology, Lenhart is a mother of two, Packard is a mother of three and had a small part in the then-upcoming film My Girlfriend's Boyfriend, Franke is living in Australia with his wife and had recently finished filming a television pilot he created himself, Kwan (who became tongue-tied and blushed after being introduced) had toured with the traveling production of the musical Avenue Q and did a lot of voice acting (including the character Suki from the Nickelodeon animated series Avatar: The Last Airbender), and Cade works with the company Oxcyon and had a couple of films coming out that summer.
In February 2015, the Saved by the Bell cast was finally reunited (excluding Dustin Diamond and Lark Voorhies) and reprised their roles for a sketch which had Jimmy as a new student at Bayside High, and revealed Zack Morris had impregnated Kelly Kapowski (Tiffani Thiessen is pregnant in real life).
Guest players have included Jason Sudeikis (November 2012),[78] David Duchovny (January 2013),[79] Joel McHale (February 2013),[80] Tom Cruise (April 2013),[81][82] Seth Meyers (August 2013),[83] and Edward Norton (October 2013).
Jimmy made signs for the audience to hold up, gave them T-shirts, had their pep band play on the show, did a brief history of the school, and did an interview via satellite with Head Coach John Shulman.
He also reviewed a list of notable graduates, which includes Dennis Haskins (most known as Mr. Belding from the TV series Saved by the Bell) who made an appearance on stage in support of his alma mater and gave Jimmy a UTC hat.
In the run-up to the 2010 midterm elections, Jimmy had five Golden Retriever puppies with human first and last names (Roger Blain, Brian Johnson, Kyle McAdams, Lisa Armstrong, and "troublemaker" Gary Frick) act as "pundits" to predict the winner of various races by choosing which of two bowls of dog food to eat from (blue for the Democrat and red for the Republican).
In the theme park attraction Race Through New York Starring Jimmy Fallon at Universal Studios Florida in Orlando, the Golden Retriever puppies make an appearance, carried inside a basket by Sara's stepdad, Gary.
Jimmy enlisted the help of Zac Efron, Jesse Eisenberg, Howie Mandel, Jack McBrayer, Patton Oswalt, Maya Rudolph, Jason Segel, Martin Short, T.I., and Brian Williams to recite a shortened version of the poem A Visit From St. Nicholas in a Mad Libs fashion.
'Twas the night before Christmas, when all thro' the house Not a creature was stirring, not even a Swiffer (Mandel); The stockings were hung by the chimney with care, In hopes that Rod Carew (Oswalt) soon would be there; The children were nestled all snug in their beds, While visions of sweet and sour shrimp (T.I.)
danc'd in their heads, And Mama in her performance fleece (Eisenberg), and I in my cap, Had just settled our brains for a long winter's crap (McBrayer) — When out on the lawn there arose such a caw (Short), I sprang from the bed to see what it be (Williams).