"Bitches to Rags" is the second episode of the third season of the Adult Swim original series The Boondocks. It originally aired on May 9, 2010.
Granddad wakes to find a repo man attempting to repossess Dorothy, his car. It turns out that the repo officer is taking the wrong car from the wrong house; he was looking for rapper, Thugnificent's home.
Thugnificent is preparing to release his first album in four years, "Mo Bitches Mo Problems". Riley visits Thugnificent's house to play video games and notices that Thugnificent's home is in total disarray, the landscaping is overgrown with weeds and tall grass. Thugnificent assuages Riley by stating that everything is fine, faking a phone call with Warren Buffet, where he falsely states that he will let him borrow $8 Billion. When Riley turns on the television, he sees the video for 15-year-old rap sensation Sgt. Gutter's "Crank That Artichoke", and begins doing the dance associated with the song. A frustrated Thugnificent then tells Riley about his new album, and plays him some new songs. Riley is dismayed when he hears that every song on the album uses the Auto-Tune effect, but Thugnificent notes that it's the hottest sound.
Thugnificent is a guest on the DJ Vlad radio show, where Vlad constantly reminds the audience and Thugnificent that he's old. After Thugnificent reminds everyone that he's still a fan of The Notorious B.I.G. - a fact that makes him look even older, he pulls out a sheet of paper and reads a list of current rappers that he may or may not be a fan of. Absent from that list is Sgt. Gutter, whom Thugnificent despises, starting a rap beef. Thugnificent pleads to his MySpace fans to support his album and beef with Sgt. Gutter. It is a colossal failure in record sales. His record label later drops him. Later, Sgt. Gutter responds to Thugnificent's internet video with a response of his own on YouTube, calling Thugnificent old. He supposedly calls Thugnificent's mother, who reprimands Thugnificent for using foul language.
Macktastic has since gone back to pimping, and Flonominal has gotten himself a regular office job. He visits Thugnificent and tells him to do the same at the same place he is working. Thugnificent appears at an interview, where he tells the hiring manager that he is only getting a job as a temporary measure, because his rap career will blow up again, and he will take Flonominal with him. The hiring manager looks up Thugnificent and notices that the two were both rappers in the Lethal Interjection Crew, and not only refuses to hire Thugnificent, but has Flonominal fired at the same time (mostly for not mentioning his rap career in his resume).
Down to his last resort to pay for his $132,000 mortgage payment owed to the IRS, Thugnificent decides to start selling crack. The problem with this venture is that neither he nor Leonard, Thugnificent's roommate, know how to actually make crack. The two try watching a rap music video made by JJ the genius for the instructions before finally looking up the procedure on Wikipedia. Thugnificent's first night out selling crack is a disaster, with one sale having to be refunded due to the crack rocks being burned. A young fan also notices Thugnificent, which humiliates him as the fan questions why his latest album used so much Auto-Tune. Thugnificent gives up. He makes one last desperate call to a "Steve" at a record label that once tried to sign him. Steve offers him $150,000 as an advance for a new Thugnificent album, rather than actually buying cocaine. With Ed Wuncler III and Leonard in tow, Thugnificent visits Steve's home, where a young boy is randomly setting off fireworks. Ed becomes annoyed that he's not there for a drug deal and learns that he's not going to be making any money. He starts a gunfight, where he is shot, (Since Ed constantly wears a bullet-proof vest, he is not wounded). Thugnificent runs from Steve's house, his record deal off the table, and passes out in the street in front of the Freeman's home. Granddad finds him and brings him inside where the family pleads with Thugnificent to get a job again. Thugnificent then laments to Robert and the Boys that he always wanted to be a rapper and that even he himself, was amazed he pulled it. But had hoped it would last longer. Realizing he's not going to be able to compete with the younger crowd coming, Thugnificent ultimately understands that his career is over. The IRS later visits Thugnificent at his home and begins foreclosure proceedings.
The next scene shows Riley excitedly waking up to hear Thugnificent's "Bootie Butt Cheeks" blasting from a car stereo outside. We see Thugnificent ghost-riding his delivery truck. He is working as a delivery man - his trademark hair now cut - and delivering a package to the Freeman home. Leonard is working with him and acting as a cameraman. When Riley wonders why, Thugnificent - now going by his given name of Otis Jenkins - tells him that he's filming a reality show. Since "the music industry is dead", Otis is going for "that Flavor Flav" money. Thugnificent calls out for Granddad to see the new him. In reaction, Granddad (annoyed by all of the noise interrupting his sleep) throws a book at Leonard's camera, ending the episode.
- Thugnificent often uses the phrase "no homo", which is a phrase coined by New York rapper Cam'ron. It is used to erase possible misconception about the person's sexuality when saying something that could be misconstrued as gay. For example, when Flonominal gets fired and walks away, Thugnificent yells "I love you man..... no homo".
- The Scenes in which Thugnificent shouts out Damn,Damn,DAMN is a reference to the closing moments of an episode of Good Times where James died and Florida Evans has finally accepted the fact that her Husband is really gone.
- Sgt. Gutter is a parody of teenage rapper Soulja Boy Tell 'Em. His song "Crank That (Artichoke)" and its accompanying dance is a reference to Soulja Boy's smash hit "Crank That (Soulja Boy)".
- Sgt. Gutter's feud with the "old" rapper Thugnificent is a reference to the real-life feud Soulja Boy had with rapper Ice-T. The two also traded internet videos to further their beef.
- "Mo Bitches Mo Problems", Thugnificent's latest album, is a play on the name of The Notorious B.I.G.'s single "Mo Money Mo Problems".
- The episode's title references Thugnificent's first appearance in the series in the episode "The Story of Thugnificent", where MTV aired a documentary about Thugnificent called Rags to Bitches.
- In the scene where Thugnificent is selling crack, one of the characters trying to buy from him is similar to Tyrone Biggums, a crack addict that Dave Chappelle portrays on Chappelle's Show. Charlie Murphy, a regular on Chappelle's Show, was listed as a guest star in the episode credits. He does the voiceovers for Ed Wuncler III.
- The Scene where Thugnificent is trying to sell drugs to Steve is a homage to the film Boogie Nights staring Thomas Jane and Mark Wahlberg, right down to the Asian kid throwing firecrackers.
- Thugnificent strays from his original style and creates an entire album using "auto-tune". This is similar to Kanye West's album 808's and Heartbreak.
- The scene where Thugnificent is trying to sell crack to the record producer is a parody of a scene in Boogie Nights where Mark Wahlberg's character attempts to sell fake cocaine to a rich cocaine addict.
- In the end when Thugnificent gets a job at UPS is a reference to the infamous Notorious B.I.G. line from "Flava in Ya Ear Remix". This version of the song also features LL Cool J and more importantly Busta Rhymes, who is normally featured as the voice of Flonominal, however he is voiced by Kevin Michael Richardson in this episode.
- At the end, Riley refers to himself as "The Fundraiser" as seen in "The Fundraiser" episode later on.
- Also when Thugnificent tells Sgt. Gutter to "pop his Mama tittie out his mouth" that is referenced from the movie "Major Payne" when Major Payne tells Miss Walburn to pop her tittie out of Tiger's mouth and stop babying him.
- Leonard, the Lethal Interjection reject from the episode "Shinin'", is revealed to be not only living in Thugnificent's home, but also the only one in the house earning money to pay the bills.
- In another continuity from Shinin', Leonard says if Lethal Interjection someday goes down the gutter, that the crew would be "flippin' burgers at Wendy's." In this episode, he actually gets a job at Wendy's when Thugnificent is unable to pay for his house.
- In what can only be considered foreshadowing—while taping Thugnificent's reality show, Riley says, "Young Reezy!! AKA 'The Fundraiser', nigga!", which is a reference to a future episode, "The Fundraiser".
- Though Flonominal appears in this episode, he is not voiced by Busta Rhymes. Macktastic does not appear in this episode.
- According to his business card, Flonominal's real name is Derrick Cornish.
- This is the first episode of the series where Huey has no speaking parts.
- This is the third episode in the series where Riley has taken narrating duties, the first being in the Season 1 episode "The Story of Gangstalicious" and the second being the season 2 episode "Shinin'".
Leonard Pierce of The A.V. Club graded the episode a B, writing that although the episode's satire was strong, it felt directionless and, by not tying into the Freeman family, suffered "a lack of any way to tie its keen parodies of the pitfalls of the gangsta-rap lifestyle to the ordinary human level."