On February 1, 2020, Ridgio released Twenty V Winters, which he introduced at a silent listening party in Chicago's Lincoln Park. NPR's Vocalo Radio placed Twenty V Winters' "Have You Ever" in its Poised to Breakthrough list. In this album, he displayed how he felt about the connections with the people who are closest to him, throughout his life. In an interview with Dark Matter Publications, Ridgio expressed, "I want them to listen to it beginning to end because it tells a story. I hope that people from song number one to song 25 would just listen to it, because it is cohesive. We're in an age right now where people just put a bunch of songs together and just label it an album and that's not what [my music] is." The COVID-19 pandemic followed right after the release of his album. He expressed that the pandemic hindered him with making music videos and promoting the album. Ridgio followed up mid 2020 with his album We Made It. It is what he calls an Interactive Project, where he had fans pick the producers, songs, and features on the album. In an interview about the project, Ridgio said, "It's called 'We Made It' because we made the project together. From start to finish, me and all of my supporters made the whole thing. From the concept, to production, to who's on it… It was also supposed to tie in quarantine, but we didn't really get out of quarantine fully, but maybe in the future it will!".
