"The Worst That Could Happen" is a song with lyrics and music written by singer-songwriter Jimmy Webb. Originally recorded by The 5th Dimension on their 1967 album of nearly all-Jimmy Webb songs, The Magic Garden, "The Worst That Could Happen" was later recorded by Johnny Maestro & the Brooklyn Bridge and reached the Billboard Hot 100's top 40 (at #38) on 4 January 1969, peaking at #3 on 1-8 February 1969.

The song depicts a man wishing well to a woman with whom he is still in love, but because the man was unwilling to settle down, she left him and is about to marry someone else who is more stable; the singer accepts the marriage but still feels that it is "the worst (thing) that could happen to (him)." It has been stated that, along with "MacArthur Park" and "By The Time I Get to Phoenix", "The Worst That Could Happen" is about a relationship that Webb had had with a woman named Susan.

The song is noted for the quoting of Mendelssohn's "Wedding March" from the incidental music to "A Midsummer's Night's Dream", which is heard at the song's end, which in the Brooklyn Bridge version, is played by a handful of trumpets, while in the Fifth Dimension version, is played by an electric organ.

According to BMI (Broadcast Music Inc.) the legal title of the song is "Worst That Could Happen".

The song appeared on the list of songs deemed inappropriate by Clear Channel following the September 11, 2001 attacks specifically and inexplicably listing the Johnny Maestro & the Brooklyn Bridge version, but not the 5th Dimension version, despite their note-for-note similarity.

Jimmy Webb recorded his own version of the song for his 1996 album Ten Easy Pieces.

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