Street Musician

A street musician is one who plays an instrument anywhere large numbers of people congregate and/or pass by (such as at a busy streetcorner or subway station) in hopes that people will drop money; usually, his/her instrument case serves as place to gather said money. A common gag is to have the musician be purposely terrible and let people pay him to stop.

Sub-Trope of Street Performer, Wandering Minstrel, Super-Trope of One-Man Band and Organ Grinder.

Anime & Manga

 * Mahou Tsukai Ni Taisetsu Na Koto ~Natsu no Sora~ has Yasuko, who sings and plays guitar across Shitokitazawa station in Tokyo. Main character Sora loves listening to her performances, and Yasuko's songs form a loose commentary on what happens in the series. Yasuko even interacts directly with the main cast later on and is included in the Distant Finale.

Film

 * A violin player is seen playing the old animated Spider Man theme in the second movie.
 * Jamie Foxx's character (a bum who happens to be a virtuoso violinist) in The Soloist.
 * In Zorro's Fighting Legion one of the baddies is a Dreadful Musician mariachi who uses his busking as a cover for relaying secret messages.
 * In Mary Poppins, buskers play back-up during "Supercalifragilisticexpialidocious". Bert also appears as a One-Man Band in the opening scenes.
 * There's a street band in Halloweentown on The Nightmare Before Christmas.
 * In Cool Runnings, Sanka tries to collect money for the bobsled team by singing in the street. He only made a dollar and sixteen cents, and most of that came from a man who said, "I'll pay you a dollar...to SHUT! UP!"

Literature

 * The harmonica-player in Moving Pictures.

Live-Action TV

 * One time on Mad About You Paul got some change for a pay phone (remember those?) from a street performer by putting a dollar in the guitar case and taking coins out. He was looked at askance by the performer and passers-by, who thought he was just taking money out. He made a big deal about putting in a five and just taking a little change.
 * Mr. Bean used this trope a few times. Once in the TV episodes he wanted to drop money into a busker's saxophone case but discovered he had no loose change, so he laid down his handkerchief and danced along to the sax music. When a lady walked by and dropped a coin onto his handkerchief, Mr. Bean transferred it into the sax case and continued along on his way.
 * Mr. Bean does some more busking in the 2007 film Mr. Bean's Vacation to several songs playing from a borrowed stereo, culminating in a lip-synched performance of Puccini's "O Mio Babbino Caro."
 * The Monk episode "Mr Monk and the Very Dead Man" concerns a murdered street musician. The other police become convinced that it's the work of a serial killer in the making, one targeting street musicians. So they have Lt. Disher pose as a busker to draw the killer out.

Newspaper Comics

 * Floyd in Beyond The Black Stump, whose playing is so terrible people are more likely to pay him to stop -- even when he's playing air guitar.
 * Little Orphan Annie: Annie worked as this together with "Uncle" Dan.

Video Games

 * Fable 2 - being a street musician (by playing a Guitar Hero-style rhythm game) is one way you can earn money.
 * In Steambot Chronicles, being a busker is a valid choice for making money.
 * In The Sims 1, the first job a Sim in the Music career has is "Subway Musician." Averted in The Sims 2, though; there a Musician sim starts off as a Record Store Clerk. In The Sims 3, anyone who can play a guitar can play for tips, regardless of their job.

Webcomics

 * The buskers in Questionable Content, who even get into a turf war at one point (it's Played for Laughs).
 * In Sinfest, Squidley finds it far more effective than merely begging.

Western Animation

 * There's a Pixar Short called "One Man Band", where a little girl wanting to toss a coin in a fountain to make a wish is accosted by two street musicians, each wanting her coin. They finally make her lose it and she demands to be compensated. They give her a violin, and when she proves to be a virtuoso, someone tosses her a bag full of coins.
 * An episode of Tom and Jerry Tales has Tom and Jerry competing against each other on opposite street corners, performing music for money.