Many recent alumni come from various reality shows including Survivor, The Amazing Race, Are You the One?, Big Brother, Ex on the Beach, Vanderpump Rules and Love Island as well as non-reality entertainment and sports programs.

Sporadically throughout the course of each episode, various contestants are seen privately expressing themselves through reality TV confessionals about the events taking place on the show.

[5] Over time, a playful rivalry developed between the cast of Road Rules and The Real World, with the former occasionally attempting to prank the latter while it was in production.

The episode brought in high ratings and this set ideas in motion to produce the spin-off series.

[7] The series started airing in April 1998 as Road Rules: All Stars, and featured cast members from five seasons of The Real World.

Another face-off called AquaGames, hosted by Kit Hoover and Mark Long, was between The Real World: Seattle and Road Rules: Down Under and aired as part of those shows later in 1998.

[8] Following the successful boom of reality television in the new millennium, from shows like Survivor, producers decided to add new elements to the series.

[14][15][16][17][18][19] In 2020, Road Rules: USA – The First Adventure alumnus Mark Long started asking his social media followers if they'd be interested in seeing former cast members of The Challenge coming together for a new version of the series.

After his idea went viral, he announced a partnership with Bunim/Murray Productions to further develop his project and began gauging interest from potential former cast members.

[22][23][24][25][26][27] On May 22, 2023, following the conclusion of World Championship, CBS announced that a second season of The Challenge: USA would premiere on August 10, 2023.

[28] On June 27, 2024, it was announced that a Swedish version of The Challenge would be airing on TV4 starting on August 12, 2024, marking the first series in the franchise to be produced outside of Bunim/Murray Productions.

Fresh Meat alumnus Evan Starkman and The Real World: Key West alumna Paula Meronek served as broadcasters, with T. J. Lavin as the host.

[37][38] Camila Nakagawa, a contestant of the winning team, went on to appear on future challenges, with her debut season being Cutthroat.

The docuseries focuses on eight cast members visiting their hometown and sharing stories about their career and upbringing.