Editor’s note: How do you define a season of SNL in just ten clips? That’s the task we gave Jon Schneider of LateNighter’s podcast partner the Saturday Night Network, whose season-by-season video series “Everything You NEED to Know About Saturday Night Live” has just reached Season 27.
Few seasons in Saturday Night Live history were shaped more by events outside Studio 8H than Season 27.
Originally set to lay the groundwork for a new era with fresh cast members like Amy Poehler and Seth Meyers, the season instead became forever intertwined with the aftermath of September 11th. Faced with the challenge of helping a grieving nation laugh again, SNL opened the season with one of the most significant moments in the show’s history and concluded it with a goodbye to an all-time great in Will Ferrell.
Here are ten essential moments from SNL Season 27:
1) 9/11 Tribute (Sep. 29, 2001 – S27 E1)
One of the defining episodes in SNL history, the decision to return to the air less than three weeks after the attacks set the tone not just for Season 27, but for how TV would approach comedy in the months that followed. The opening featured New York City Mayor Rudy Giuliani, first responders, Paul Simon performing “The Boxer,” Lorne Michaels asking “Can we be funny?” and Giuliani responding “Why start now?” It remains one of the clearest examples of Michaels and SNL finding the right tone at an almost impossible moment.
2) Presidential Address (Oct. 6, 2001 – S27 E2)
Just one year earlier, SNL had navigated an extended, contentious election cycle that saw Will Ferrell playing George W. Bush as a frat-boy type opposite Darrell Hammond’s monotone, emotionless Al Gore. Following the events of 9/11, Ferrell’s first portrayal of Bush in Season 27 took a much different tone, delivering a stern message to Osama bin Laden: “Buddy, you screwed up big-time.”
3) Show Your Patriotism (Oct. 6, 2001 – S27 E2)
Ferrell had another huge moment in the season’s second episode, appearing in an office sketch where coworkers are asked to wear something patriotic to work. Ferrell appeared at dress rehearsal wearing very short American flag shorts, then decided to hike them up even further for the live show, revealing far more of himself than his fellow castmates, host Seann William Scott, and the Studio 8H crowd expected to see that night.
4) Drew Barrymore Monologue (Oct. 13, 2001 – S27 E3)
Just when life seemed to be inching back toward some version of normal, anthrax was discovered inside NBC News, causing an evacuation of 30 Rockefeller Plaza. There was uncertainty over whether SNL would be able to air, but host Drew Barrymore and Lorne Michaels decided the show should continue. In a memorable monologue, Barrymore addressed the trials and tribulations of putting on the show that week, with her then-husband Tom Green joining her for the segment.
5) e.p.t. (Nov. 3, 2001 – S27 E4)
With so much attention on the major outside events shaping the start of Season 27, it would be easy to overlook just how quickly Amy Poehler broke through. In only her fourth episode, Poehler appeared in six sketches, including this pregnancy test commercial opposite Seth Meyers—her future Weekend Update co-anchor. Her fast start would lead to her becoming just the third featured player to be promoted during her first season, following Harry Shearer in Season 5 and Eddie Murphy in Season 6.
6) Giuliani on Update (Dec. 15, 2001 – S27 E9)
With his tenure as the 108th mayor of New York City set to end on December 31, 2001, Giuliani returned to Saturday Night Live for the final episode of the year, joining Tina Fey and Jimmy Fallon to sing “Will You Still Love Me Tomorrow.” Though less remembered than the 9/11 tribute from the season premiere, the moment is a reminder of how Giuliani was viewed at that specific point in time, as he prepared to move on to the next chapter of his life.
7) Music International (Jan. 19, 2002 – S27 E11)
One of the most popular hosts of the era kicked off his SNL tenure when future five-timer Jack Black hosted the second episode of 2002. For the final sketch of the night, Black performed an epic rendition of “Happy Birthday,” turning the traditional birthday song into a gothic rock opera.
8) Jon Stewart on Update (Mar. 9, 2002 – S27 E14)
In an episode hosted by Jon Stewart, the Daily Show host took a familiar spot behind a desk when Jimmy Fallon told the first-ever “tree frog” joke in SNL history. The tree frog joke would be used from 2002 to 2013, with an anchor starting a joke about a new study on tree frogs before being interrupted for another gag. In this case, Fallon had a leg cramp, causing Stewart to come in and replace the Update anchor.
9) Dame Maggie Smith on Update (Mar. 16, 2002 – S27 E15)
Host Ian McKellen played Dame Maggie Smith on Weekend Update, leading to an unforgettable kiss between McKellen and Fallon. “Maggie Smith should shave!” The bit was one of several highlights from an episode that went on to win the Emmy for Outstanding Writing for a Variety Series, ending SNL’s drought in the category dating back to 1989.
10) Will’s Final Show (May 18, 2002 – S27 E20)
One of the all-time great cast members received the first official goodbye sketch in SNL history, with each cast member taking a moment to say goodbye to Will Ferrell. Joining the cast in the fall of 1995 after the show’s turbulent 20th season, Ferrell is widely credited with helping lead SNL’s late-’90s rejuvenation. The sketch was an emotional bookend to an emotional season for Saturday Night Live, leaving the show to face the question of what the post-Ferrell era would look like.
For more on SNL Season 27, watch the latest installment of the Saturday Night Network’s “Everything You NEED to Know About Saturday Night Live.”
