| 2008 | Self-released mixtape 'A Kid Named Cudi' caught Kanye West's ear and earned Cudi a deal with West's GOOD Music label, with breakout single 'Day 'n' Nite' driving the buzz. |
| 2009 | Debut studio album 'Man on the Moon: The End of Day' was certified Gold and made 'Day 'n' Nite' a mainstream crossover, anchoring a sound that merged hip-hop with introspective psychedelia. |
| 2010 | Second album 'Man on the Moon II: The Legend of Mr. Rager' peaked at number three on the Billboard 200, broadening his audience beyond hip-hop into alternative and rock circles. |
| 2013 | 'Indicud' debuted at number two on the Billboard 200, becoming Cudi's highest-charting album across multiple charts and reinforcing him as a multi-genre headliner. |
| 2018 | Formed supergroup Kids See Ghosts with Kanye West, releasing a self-titled album that critics cited as one of the year's strongest collaborative records. |
| 2020 | 'Man on the Moon III: The Chosen' debuted at number two on the Billboard 200, completing the trilogy a decade in the making and earning 144,000 album-equivalent units in its first week. |
| 2021 | Amazon documentary 'A Man Named Scott' offered an intimate portrait of his mental health journey and creative evolution, deepening the connection with a global fanbase. |
| 2022 | Co-created and starred in the Netflix animated special 'Entergalactic' alongside its companion album, with the dual project debuting in the top 20 of the Billboard 200. |
| 2024 | Ninth studio album 'Insano' reached number five on Billboard's R&B/Hip-Hop chart with guest turns from Travis Scott, ASAP Rocky, Pharrell Williams, and Lil Wayne. |
| 2026 | Launched the 33-date 'Rebel Ragers' North American arena tour with M.I.A., Big Boi, and A-Trak among special guests, playing amphitheaters and outdoor sheds across the U.S. and Canada. |
