A History of Short Words

From the New York Times Crossword Puzzle

SICKO

Sat, 15 Mar '25
2007 Michael Moore documentary with the tagline "This might hurt a little"
Mon, 3 Feb '25
Person with a twisted mind
Wed, 10 Jan '24
2007 Michael Moore documentary about health care
Sun, 7 Nov '21
"___ Mode" (2018 #1 hit for Travis Scott)