The 25 Best 'SNL' Players of the Last 25 Years: #5-1

On February 9, 1991 — 25 years ago this month — Adam Sandler made his Saturday Night Live debut as a featured cast member in Season 16. And we thought that was a great excuse to take a look back at the past quarter-century of SNL history and rank the 25 best cast members who’ve joined the show since Sandler did. We debated each nominee’s on-air performance only based on longevity, versatility, cultural impact, and overall magnificence, and came up with the following list. Live, from New York… it’s the 25 best SNL cast members of the last 25 years.

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5. Norm Macdonald (Seasons 19-23)
Why He Made The Cut: Probably the most fearless of all the “Weekend Update” anchors, Macdonald made cutting jokes about celebrities including O.J. Simpson and Woody Allen so fierce, they drew gasps as well as laughs. In sketches, his impersonations of Sen. Bob Dole and Burt Reynolds were impeccably accurate, but never without an element of Macdonald’s own laconic personality intentionally shining through. In this, he was one of the quirkiest, most unpredictable SNL cast members ever, and thus a polarizing figure. So polarizing, he was fired as “Update” anchor by NBC West Coast president Don Ohlmeyer for being “not funny.”

Signature Moment: Macdonald returned to the show as a host in 1999, and turned his opening monologue into a typically whimsical yet pointed meditation on his history on SNL, including the Ohlmeyer “not funny” remark, musing that, since he’d been asked back to host the show, it must mean “I haven’t gotten funnier — the show has gotten really bad!” —Ken Tucker

4. Kristen Wiig (Seasons 31-37)
Why She Made the Cut: A supremely quirky chameleon, Wiig has to go down as an all-time SNL great, thanks to the wide swath of characters she brought to life. From the demonically cheerful Target Lady to the blasé Valley girl of “The Californians” to her wicked celebrity impressions (our favorites: Kathie Lee Gifford and Suze Orman), Wiig transformed herself to find the funny in every situation. Sure, a few of her characters wore out their welcome (Gilly, anyone? No? No takers?), but Wiig never did.

Signature Moment: We could dismiss The Lawrence Welk Show’s Merrell Sisters and Wiig’s baby-handed, malformed sister Dooneese as a one-joke premise… but man, what a joke. With a face made for radio, Dooneese steals this 2008 sketch by adding her own horrifying lyrics to her sisters’ cutesy songs — when she’s not chasing bubbles with her tiny hands, that is. —Dave Nemetz

3. Bill Hader (Seasons 31-38)
Why He Made the Cut: SNL’s most reliable bringer of the funny is Bill Hader. This contemporary heir to Phil Hartman has it all: an extensive gallery of spot-on celebrity impressions from A (Alan Alda) to V (Vincent Price), recurring characters that took on lives of their own (in an earlier era, you just know that Stefon and Vinny Vedecci would have gotten their own feature films), and an Everyman appeal that immediately endeared him to the cast and audience alike. Lorne Michaels once famously told Hader that he could work at SNL for as long as he wanted. If we’d had a say, it would have been forever.

Signature Moment: Stefon is Hader’s most famous character, but Italian TV personality Vinny Vedecci is his most distinctly Hader-esque creation. Modeled after an Italian man he overheard in line while waiting to see Steven Spielberg’s 2001 film A.I., Vinny perfectly encapsulates his creator’s many talents: impersonator, improviser, and serious film buff. The delight on his face sitting across from Robert De Niro, riffing with the screen legend of Taxi Driver and The Deer Hunter, is 100 percent genuine. —Ethan Alter

2. Will Ferrell (Seasons 21-27)
Why He Made the Cut: It’s not hard to see why this beloved SNL funnyman landed in the runner-up spot on our list. From his portrayals of overly-enthusiastic Spartan cheerleader Craig, to a fictional Blue Oyster Cult member named Gene (gotta have more cowbell!), to his hilarious impersonations of Harry Caray, George W. Bush, and Janet Reno, Will Ferrell is the man behind some of the most memorable characters ever seen on the late night sketch comedy, and he has the Emmy nod to prove it.

Signature Moment: Ferrell’s most iconic SNL sketch had him portraying an exasperated Alex Trebek in a 1999 Celebrity Jeopardy! spoof. The comic was joined by Jimmy Fallon (as French Stewart), Darrell Hammond (as Sean Connery) and Norm Macdonald (as Burt Reynolds), playing the straight man to three idiotic contestants while introducing inane Jeopardy! categories like “Movies that Start With the Word Jaws” and “Your Ass or a Hole in the Ground.” Ferrell keeping a straight face through this sketch is a miracle, especially when Reynolds renamed himself “Turd Ferguson” and Connery wrote “Suck it, Trebek” for his Final Jeopardy! wager. Ferrell’s Trebek impersonation is such an integral part of SNL history that he reprised the role for the show’s 40th anniversary special last year. —Victoria Leigh Miller

1. Amy Poehler (Seasons 27-34)
Why She Made the Cut: Poehler’s SNL tenure began inauspiciously, overshadowed by seismic real-world events; she and fellow new cast member (and future “Weekend Update” co-anchor) Seth Meyers made their debuts as featured players on the first episode following 9/11. But Lorne Michaels clearly recognized that he’d found someone special: by the season’s halfway point, Poehler had been bumped up into the main cast. She’s one of only three performers to achieve a rare mid-year promotion (the other two being Eddie Murphy and Harry Shearer), and the very first to be nominated for an Outstanding Supporting Actress Emmy in 2008. On a show where the most successful performers tend to fall into two groups, “Stars” and “Utility Players,” Poehler effortlessly moved back and forth between camps, anchoring sketches (as young Kaitlin, one-legged reality show contestant Amber, “Bronx Beat” co-host Betty Caruso, Dakota Fanning, or Michael Jackson) and also providing invaluable back-up support. That’s why she’s the greatest SNL performer of the past quarter century. Yes, really.

Signature Moment: “Editorial Response” (Mar. 1, 2008)
Poehler’s Hillary Clinton impersonation won her numerous fans… up to and including the actual Hillary Clinton, who appeared alongside her doppleganger in a hilarious “Editorial Response” to a debate sketch that pitted Poehler against Fred Armisen’s Barack Obama. Besides the delight in seeing these two share the screen — in the same outfit, no less! — this clip showcases Poehler’s razor-sharp skills as an improv trained ensemble player. Watch as she cedes the spotlight to Clinton, while also making sure to slip in a joke — or demented laugh — at the exact right moment. —EA

Saturday Night Live airs Saturdays at 11:30 p.m. on NBC.