| 1979 | Self-released 'My Bologna' on Capitol Records after Dr. Demento aired the accordion-backed parody on his nationally syndicated radio show, launching a cult following. |
| 1984 | 'Eat It', a note-perfect parody of Michael Jackson's 'Beat It', hit No. 12 on the Billboard Hot 100 and earned Yankovic his first Grammy Award, turning him from a novelty act into a legitimate pop presence. |
| 1984 | Released 'In 3-D', his second studio album, cementing the template of parody and original comedy that would define more than four decades of recording. |
| 2006 | 'White & Nerdy', a parody of Chamillionaire's 'Ridin'', peaked at No. 9 on the Billboard Hot 100, his highest-charting single ever, and earned him a Grammy for Best Comedy Album for 'Straight Outta Lynwood'. |
| 2014 | 'Mandatory Fun' debuted at No. 1 on the Billboard 200, the first comedy album to reach the top spot since 1963, fueled by a viral eight-day daily-video campaign that enlisted celebrity collaborators. |
| 2018 | Launched the 'Ridiculously Self-Indulgent, Ill-Advised Vanity Tour', a 77-date intimate run inspired by MTV Unplugged in which the setlist changed every night and focused almost exclusively on original, non-parody material. |
| 2022 | Co-wrote and produced 'Weird: The Al Yankovic Story' for The Roku Channel, with Daniel Radcliffe playing Yankovic in a feature-length parody biopic that won the People's Choice Award for Midnight Madness at the Toronto International Film Festival. |
| 2025 | Released 'Weird Reboot', a new album of parodies spanning genres including K-pop, indie folk, and techno, and played a 75-date North American run that drew more than 500,000 fans across sold-out stops including Madison Square Garden, The Kia Forum, and Red Rocks Amphitheatre. |
| 2026 | Launched the 90-city 'Bigger & Weirder' North American tour with an eight-piece ensemble, a giant video wall, multiple costume changes, and special guest Puddles Pity Party, his largest production to date. |