This page is for the episode in Season 3. For the character, see Duke Ellington.
The ghost of Duke Ellington takes Nick and friends on a journey back in time to 1913; the year he lost his virginity and found his true calling.
Duke tells the boys the story of how he lost his virginity. Working his way up to his 13th year, Duke talks about his piano lessons, close relationship with mother Daisy, and paints the picture he had a middle-class life in early 1900 DC. One that didn’t have him hit too hard by the laws of Jim Crow, and he even enjoyed, on occasion, playing baseball and, a surprising fact, Theodore Roosevelt would sometimes watch him play.
But, as he grew up, there was a natural inclination to meet girls and chase skirts. After all, Maury was his hormone monster. So when he was spending a summer in Atlantic City, working as a dishwasher, he took to the rise of ragtime music, and one musician named Harvey Brooks. Someone who, per Big Mouth’s Duke, invigorated his love for learning and playing piano after his mother forced it upon him growing up. Not due to his style, however, but the women he attracted while playing.
When Duke got back home, he started playing piano at a local pool hall, and surprisingly was a hit in town. Hence the birth of Duke and how Duke says he had his first love, Jazz. Which upsets the boys, specifically Jay and Nick, for they were waiting on a sex story.
- Duke Ellington
- Daisy Ellington
- James Ellington
- Big Bowser Blakely
- Crumbum Tootles
- Mondee Tuesdee
- Harvey Brooks
- Pool Hall Girl
- Train Girl
- Ragtime Girl
- Nick Birch
- Miss Clinkskales
- Theodore Roosevelt
- Little Texas
- Andrew Glouberman
- Jay Bilzerian
- Dr. Lee Daniels
- Margaret Daniels
- Archdick Ferdinand
- Harriet Tubman
- Featuring Ludacris (Cameo)
- Coach Steve (As Coach President Teddy Roosevelt Steve)
- Half and Half (Non-Speaking Cameo)
- Church Girl (Non-Speaking Cameo)
- Charlie Chaplin (Non-Speaking Cameo)
- Buster Keaton (Non-Speaking Cameo)
- Aretha Franklin (Non-Speaking Cameo)
- Louis Armstrong (Non-Speaking Cameo)
- Dizzy Gillespie (Non-Speaking Cameo)
- Edna Ellington (Non-Speaking Cameo)
- Mercer Ellington (Non-Speaking Cameo)
- Missy Foreman-Greenwald (Mentioned)
- This episode is mostly a flashback episode, where Duke Ellington details his backstory.
- The theme song has been edited to emulate a 1910's vaudeville song.
- Coach Steve appears as Theodore Roosevelt.
- Duke Ellington breaks the fourth wall to tell the audience to look up Theodore Roosevelt watching Duke Ellington playing baseball, to prove to them that he wasn't making that up.
- Despite most of Duke's story being fabricated, this part was actually true.
- Duke Ellington lost his virginity to an unnamed girl on a train.
- Jessi does not appear in this episode. However, a 1910's version of her named Margaret Daniels does appear in Duke Ellington's flashback story.
- This is the second episode not to feature Jessi after "Florida".
- Nick does his history report on Duke Ellington after switching over from Harry Houdini to him at the end of the previous episode, "How To Have An Orgasm".
- Duke pronounces "Google" as "Joojle", just like Connie did in the previous episode.
- Nick brings up his "Big Dick Boy" joke from "Drug Buddies" again.
- Jay refers to having sex as "making thick in the warm", much like how Coach Steve did in "Steve the Virgin".
- Maurice blows off paying Duke the $5 he owes him, which was first brought up in "Pillow Talk".
- Duke Ellington's story is loosely based on the story of the real Duke Ellington. However, very much of the true story has been altered for comedic/storytelling purposes, leading to a lot of inaccuracies in his story. Obvious changes include him having Maurice as a hormone monster but a slew of more subtle tweaks to his life story have also snuck their way into the narrative, such as Duke being taught by the piano teacher, Miss Clinkskales, a closeted LGBT woman, who has a female romantic partner named Ernestine. None of this happened in real life and "Miss Clinkskales" is a purely fictional character.
- Duke Ellington says that his "Woodrow" is about to "Wilson", in reference to his penis being about to cum. This is a reference to the 28th U.S. president, Woodrow Wilson.
- Duke Ellington describes his father as being more smooth than the transition from Slavery to The Prison-Industrial Complex, referencing to how around the time Duke was alive, African-American slavery had long since ended but now African-Americans were being enslaved in a different way, by getting unfairly arrested and being forced to do similar labor in prison as penal labor.
- Miss Clinkskales says that if orgasms were money, she'd be a Rockefeller. This is a reference to John D. Rockefeller, a man known for being extremely rich and wealthy. The joke she made suggested that she's had so much sex with her lover, that she's had millions of orgasms, which would equate to millions of dollars when converted through her hypothetical comparison.
- Theodore Roosevelt rides his horse, Little Texas to the baseball field to watch Duke Ellington and his friends play baseball. This is a reference to how Roosevelt would spend most of his post-presidency days, doing leisurely activities such as watching Duke Ellington play baseball.
- Theodore Roosevelt brags that his face is going to be carved into a mountain. What Roosevelt was talking about here is Mt. Rushmore, a historical landmark, which features the faces of four U.S. Presidents, George Washington, Abraham Lincoln, Thomas Jefferson, and Theodore Roosevelt carved into them.
- Duke Ellington spoils the Game of Thrones episode, "The Rains of Castamere", by telling Nick that everybody dies in the end.
- Nick announces that he doesn't watch anything on the streaming service HBO and then asks an offscreen person if he said what they wanted him to say. Supposedly, he is talking to someone on the other side of the fourth wall, who paid him to defame HBO and further promote themselves, (themselves being Netflix), via celebrity endorsement from Nick Birch, which is also used as a smear campaign against their competition.
- James Ellington worked as the butler for a man named Lee Daniels. This is a joke on the movie, Lee Daniels' The Butler.
- Margaret's Vaginabonnet is a parody on the Pussyhat, hats worn by liberal third-wave feminists during the 2017 women's march, to protest against the presidency of Donald Trump in hopes that it would get him impeached. To make a long story short, it didn't. The pussyhat is meant to be a visual metaphor for a woman's vagina, specifically using the slang term "pussy" because of a leaked video of Donald Trump riding a bus and joking about grabbing a woman by the pussy.
- Jay mentions that he once fucked a gel insert from Dr. Scholl's, by rolling it up, sticking his dick into it, and wrapping a blood pressure sleeve around it to keep it tightly fastened onto himself.
- Dr. Lee Daniels orders a "Cocaine Cola". This is a reference to the drink Coca Cola and the false rumors about how back then, the drink contained the drug known as cocaine, which is where the drink allegedly got its name from.
- Daisy refers to the Brooklyn Bridge as "recently constructed". At the time this flashback took place (1913), the Brooklyn Bridge, which had completed its construction in 1869, had been around for 44 years, making its construction not so "recent" after all.
- As couples part ways on the train, famous 1910's vaudeville performers, Charlie Chaplin and Buster Keaton can be seen kissing each other goodbye, joking that the two were a gay couple.
- Andrew complains about how the movie La La Land got snubbed at the 2017 Oscars, in favor of Moonlight.
- Maurice compares a train going through a tunnel to a penis going through a pussy, which is a reference to an innuendo from the movie, North by North West.
- This same metaphor is played straight at the end of the episode when Duke has sex with the Train Girl on the train and the train goes through a tunnel.
- Duke gets his musical inspiration from listening to Harvey Brooks.
- The Ragtime Girl orders two "New Fashioneds", which is a reference to Old Fashioned Pale Ale. The joke here is that because this is taking place in the past, "Old Fashioned" becomes "New Fashioned".
- Maurice's penises do a reenactment of World War I called "World War Cum", starting with the assassination of Archdick Ferdinand, who is a parody on Archduke Ferdinand.
- Much like how Nick has the ghost of Duke Ellington in his attic, Duke had the ghost of Harriet Tubman in his attic, who details the story of how she escaped slavery.
- Nick says that before Donald Trump got elected, Harriet Tubman was going to be on the $20 bill. This is a reference to a protest to get Harriet Tubman's picture on the $20 bill to replace Andrew Jackson. Donald Trump spoke out against this, saying that there was no reason to do this and that it was "purely political". The mass production of Harriet Tubman dollars was intended to happen in 2020, but the Trump Administration delayed this until the year 2028.
- Additionally, Nick notes that now John Schnatter of Papa John's pizza is going to be the new face on the $20 bill. Andrew says that this makes sense. The reason for this is because of a controversy surrounding Schnatter in 2018-19, where he allegedly used the N-word, which led to him being forced to resign from his job as CEO of his own chain of restaurants. The joke here is that Donald Trump is a racist who would rather a racist white guy get representation over a historically heroic African-American woman.
- Teddy Roosevelt mixes up his wife, Elanore Roosevelt with American talk show host, Ellen Degeneres.
- During the montage of Duke Ellington's soon-to-be success in life, Duke is seen marrying his wife, Edna Thompson and later teaching his son, Mercer Ellington how to play the piano.
- Duke Ellington gets his face put on the cover of Time magazine. This is a depiction of an actual issue of Time magazine, that featured Duke Ellington in the same position he was in the show.  The show even goes as far as to date the cover with "August 20th, 1956". Although this date was not printed on the cover like it was on the book, that is the release date of the magazine issue in question.
- Duke Ellington eats dinner with Aretha Franklin, Dizzy Gillespie, and Louis Armstrong.
- Duke Ellington gets awarded a Spingard Award from the NAACP in 1959.
- Duke Ellington assumes Nick is going to copy and paste his report from Wikipedia.