22: "We're Sending Our Love down the Well"

Various "We're Sending Our Love Down the Well", was a "Live Aid" style video spearheaded by Sting and Krusty to raise money to rescue a boy called Timmy O'Toole, who was stuck down a well. Timmy O'Toole, was in fact Bart Simpson's radio speaker.
Troy McClure, Scott Christian, Stephanie the weather girl, Bleeding Gums Murphy, Mayor Quimby, Princess Kashmir, Sting, Sideshow Mel, McBain, Dr Marvin Monroe, Lance Murdock and the Capitol City Goofball all participated in the record.
The song reached number one, but was replaced by "I Do Believe We're Naked" by Funky C Funky Do after it was found that Timmy O'Toole did not exist. 8F11 - Radio Bart

--- Song selector --- "A Boozehound Named Barney" "Baby on Board" "Bagged Me A Homer" Bart's Army Marching Song Canyonero Jingle "COPS: In Springfield" Theme "Cut Every Corner" "Flaming Moe's" Song Homer Simpson's Theme "Itchy and Scratchy" Theme Jebediah Springfield Theme Lisa's Protest Song Mediocre President's Song Monorail Song "New Orleans!" "Oh Wacking Day" "See My Vest" "Slanderous Mambo" Stonecutter's Song "Talkin' Softball" "Those Were the Days" "We're Sending Our Love Down the Well" "Who Needs the Kwik-E-Mart" "You're Wife Don't Understand You"