The Simpsons: Greatest Hits is a collection of episodes that was released on November 8, 1999 on VHS and on September 8, 2003 on DVD as part of the series The Simpsons Classics. This collection was specifically themed around episodes of significant content in the series' history, and included the justification for why each episode was featured in the information on the back of the case.
- "Simpsons Roasting on an Open Fire" - The 1st episode
- "Sweet Seymour Skinner's Baadasssss Song" - The 100th episode
- "Trash of the Titans" - The 200th episode
- "Bart Gets an "F" " - The highest rated episode
- "Lisa's First Word" - Maggie speaks for the first time