Generation finds Caskey at new creative heights. The Cash Money artist speaks on an array of topics on the album, including loneliness, humility, and retrospection. Three spoken-word interludes serve as precursors to the themes discussed in the following songs and separate the project into acts. Braggadocious “mumble rap”, chaotic politics, and the state of Caskey’s generation are just a few of the issues he tackles here. Generation’s lead single, “Generation Y”, was dropped on February 4th, 2017. Drawing inspiration from the song, Caskey started to form a concept for the album and announced it in March. The second single, “Faith in God,” was released alongside its music video on May 28th. A tentative release window of July and a temporary album cover were revealed about a week later in early June. Promotion for the project rolled out on social media in mid-July. The month was nearing its end before the official cover was unveiled, with the project ultimately releasing on August 1st, 2017. Promotion for the project was handled by Caskey’s manager, Legit Looks. The first piece of promo was a pair of videos that feature thought-provoking speech that relates to the content of the album. The first video samples a conversation with the Indian poet and mystic Sadhguru in which he discusses the overload of information that today’s generation experiences. The second samples Eat, Pray, Love author Elizabeth Gilbert from a TED Talk in which she discusses the fear of failure and rejection. The other piece of promo involved Caskey’s fans. Cas and Legit Looks asked the fans to submit videos in which they spoke on what they thought were the most pressing issues facing their generation. Legit Looks compiled the clips into a video that they uploaded to YouTube. Many of the submissions were incorporated into the album’s songs; some of them even into their own interludes, like “Act I (Lorenzo)” and “Act II (Paco)”. Caskey himself speaks on his concerns with today’s generation on the penultimate track, “Act III (Caskey)”, before ending on “Generation Y”. Generation was originally released on Apple Music, Tidal, DatPiff, and SoundCloud, as well as on CDs sold through his website. It was later added to Spotify, Google Play, LiveMixtapes, and HotNewHipHop, among other places. Like his last two projects, there are no features. Production was handled by frequent collaborators Taysty, Anonymass, Hector Sounds, and Adam On The Track, as well as PettyBoyBeats and Dee C. The project was mixed by MixedByLex.