Colton Underwood has become one of Bachelor Nation's most notorious stars since he was chosen to lead The Bachelor season 23, and while his journey was one-of-a-kind in itself, his life after his appearances on ABC received even more attention. Like most other Bachelors, Colton was first introduced when he competed for Becca Kufrin's heart on The Bachelorette season 14. Colton later appeared on Bachelor In Paradise season 8, and although he failed to leave paradise with a significant other, he was given a third shot in September 2018 when he was announced as ABC's choice for their next season of The Bachelor.

While Colton showed some promise when The Bachelor season 23 kicked off in early 2019, it didn't take long for longtime fans to criticize Colton's journey. Although the then 26-year-old Colton and his ladies traveled to countries like Vietnam and Portugal, it wasn't until Colton's now-ex-girlfriend Cassie Randolph quit at the end that viewers became fully invested.