The U.S. men's national team has had a interesting relationship with the World Cup. After appearing in three of the first four competitions (1930, 1950, 1954), the Yanks missed the next nine before returning, in 1990, thanks to a pivotal qualifying goal by Paul Caligiuri in Trinidad & Tobago. (You can see where this is going, right?)
From there, the USMNT represented at every World Cup from 1994 to 2014, going as far as the quarterfinals in 2002 ... only to infamously miss the 2018 edition after failing to win in -- you knew it was coming -- Trinidad & Tobago.