| 1981 | Founded by Republican Senate staffers Bill Strauss, Elaina Newport, and Jim Aidala, who performed their first show as a Christmas party for the Senate Foreign Relations Committee, launching what would become America's defining political comedy troupe. |
| 1982 | Expanded to include House staffers and Democrats, broadening the troupe's bipartisan voice and beginning their transformation from office party act to professional ensemble. |
| 1989 | Began their long-running NPR radio partnership through affiliate KCRW, producing political satire specials broadcast on roughly 150 stations coast to coast, a platform they maintained for the remainder of their performing life. |
| 1993 | Released their eighth album during the Clinton Administration, part of a run of eight Clinton-era albums that became some of their best-known work and helped establish the group's reputation for skewering whoever occupied the Oval Office. |
| 1998 | Earned the endorsement of Former House Speaker Newt Gingrich, who quipped he liked it better when they made fun of Clinton, a quote the troupe adopted as one of its signature promotional lines. |
| 2000 | Surpassed 20 recorded albums while performing over 400 shows per year at venues spanning Portland, Maine to Portland, Oregon, sustaining a touring footprint rivaled by few comedy acts of any genre. |
| 2005 | Appeared on PBS television in addition to their sustained NPR radio presence, bringing their song-parody format to a national broadcast audience across small- and medium-size venues throughout the United States. |
| 2015 | Passed the 40-album mark in their catalog of musical political parody, a body of work spanning every administration from Reagan through Obama and covering Capitol Hill, the Oval Office, and global headlines. |
| 2019 | Delivered more than 400 shows across the US in their final full touring year, drawing on nearly four decades of bipartisan material that had made them the longest-running political satire act in American performing history. |
| 2021 | Announced the dissolution of the troupe after 39 years, citing the impossibility of sustaining a live-performance-only model through an extended pandemic shutdown, closing a catalog of more than 40 albums and thousands of performances. |