Looks like its that time of year again! Chance returns with the fifth season of That Time Of Year Freestyle, including the fifth artist joining the gang and the series Watty2Up! Back in October 2021 is where it all began with Chance dropping the first season not having the intentions of continuing the series. The following year in November 2022, Genius Assassin became the first artist to join the series in Season 2 which it hit New York City billboards over in Times Square. In December 2023, Cuban Connect joined the series in Season 3 which it became one of the seasons with the highest demand. The following year in October 2024 (just like Season One) Season 4 came along with 90s Baby joining the party.
Finally this year on November 30th, Chance reunites with the gang returning for a Season 5 and this time with Watty2Up as the newcomer to the series. The new Season 5 comes with many styles compared to the previous seasons. What many didn’t know, Genius Assassin being incarcerated and having his presence on the record was needed for the sake of the season while Watty2Up came with a twist. Watty2Up raps about his lifestyle and character: “If theirs a problem we coming straight wild!” while 90s Baby comes right after with a different approach: “the government tryna get rid of my people!” then after with the “Spanglish” flow & rhythm. Cuban Connect follows up right after once again rapping about his character “Stay fresh got my cubans on, two chains got me froze!” with the mastermind him self Chance entering the last verse then finishing it off with “See me at the very top of the year, its that Season 5 of that time of the year!”.
That Time Of Year Freestyle (Season 5) reaches a mid-point since its been 5 years where many think if this might still continue into more seasons. Will That Time Of Year Freestyle return for a Season 6? We will have to wait and see but it appears it will arrive in December 2026 (just like Season 3). That Time Of Year Freestyle (Season 5) featuring Genius Assassin, Cuban Connect, 90s Baby & Watty2Up is available at Reverbnation.com/Officialchance for free streaming and downloads. Its also available now on all platforms & your favorite social media platforms! That Time Of Year Freestyle Series (Ep) with all 5 seasons will soon be available on all platforms. Its Season 5 baby! OUT NOW!
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