Each week, I will be posting a list of 25 sketches from each 5 year block of the show's history (five sketches per season), a description of the sketch, and what about it that's worth checking out.
Biography (Mariel Hemingway / Blues Traveler, 09/30/1995)
What it's about: The story of how Mariel Hemingway nearly lost the role of Stephanie Wells on Central Park West to four men.
Why it's worth checking out: Central Park West was heavily promoted at the time (which accounts for Hemingway being booked for the show) but quickly cancelled and forgotten; luckily, Will Ferrell, Mark McKinney, David Koechner and Tim Meadows struggling to read lines in unison while standing together in an oversize wig and outfit is a funny enough sight outside of that specific context. This sketch also has a lot of random throwaway humor, particularly in the narration (Hemingway somehow having a congressional career, Darren Star being a one-eyed weirdo who holds meetings in caves).
The Hulk Hogan Talk Show!!! (Anthony Edwards / Foo Fighters, 12/02/1995)
What it's about: The regular features of a wrestling-themed talk show interrupt the guest host's (Will Ferrell's) attempt to have a serious interview with a former hostage (Anthony Edwards).
Why it's worth checking out: An early SNL contribution by Adam McKay with a great fake-out at the beginning (the extended and repetitive theme song giving way to Ferrell announcing “Hulk Hogan is on vacation”), and the juxtaposition of Edwards’ harrowing tale of torture against interruptions for wrestling highlights, a trivia question, fan mail, and lastly, a crude cartoon of the Hulkster saying “You’re pinned, chump!” to signal the show was out of time.
Wedding Vows (Madeline Kahn / Bush, 12/16/1995)
What it's about: David (Will Ferrell) and Susan (Madeline Kahn) read vows they wrote themselves, which contain a lot of strange and inappropriate content.
Why it's worth checking out: The vows are hilarious, ranging from the awkwardly inarticulate (“Susan, you are really good. Good like wood.”) to bizarre descriptions of heads being filled with goo (which moves Ferrell’s character to tears) and discussions of hotness and humping.
Hi-C and Turkey (Danny Aiello / Coolio, 02/10/1996)
What it's about: Insurance salesman (Danny Aiello) repeatedly insists on his potential customers (David Koechner and Nancy Walls) providing him Hi-C and Turkey.
Why it's worth checking out: An example of the “middle-aged character actor” rule on SNL, in that they tend to do the best at playing menacing weirdos. I could also see Christopher Walken playing the insurance salesman, but the bizarre specificity of Aiello’s demands and his belligerence when he doesn’t get what he wants makes it memorable.
Taddli (Phil Hartman / Gin Blossoms, 03/23/1996)
What it's about: Simple-minded daytime talk show host with a black-and-white morality (Mark McKinney) chides his guests for "sucking on the pot".
Why it's worth checking out: Years later in a Grantland testimonial, McKinney mentioned this as a favorite character of his, and one that would have been more at home on Kids In The Hall than on SNL; indeed, a dim foreigner of ambiguous nationality wasn’t going to catch on the same way the Spartan Cheerleaders or Mary Katherine Gallagher did, but this had that little bit of KITH-style weirdness to it. Bonus feature: a good chunk of the writing staff can be seen in the audience, including Paula Pell, Adam McKay, Lori Nasso, Tom Gianas, Dennis McNicholas and Cindy Caponera.
Tic-Tac-Toe (Bill Pullman / New Edition, 10/19/1996)
What it's about: The paper-and-pencil game translates poorly to the game show format, largely thanks to the use of a carpenter (Norm Macdonald) manually hanging the letters onto the board.
Why it's worth checking out: Despite Bill Pullman’s overly hammy performance as the host (“Jeeeeeeeeeaaaaack!”), this has a fun concept dominated by enduring the frustratingly slow pace of the game (which inexplicably dispenses with a chyron in favor of hammering nails into a board), Norm Macdonald playing another crotchety old man, and some technical difficulties (the X Norm hangs doesn’t seem to want to stay in place).
Mostly Used Mattresses (Martin Short / No Doubt, 12/07/1996)
What it's about: Larry Azaria (Mark McKinney) promises his inventory of stained and damaged mattresses have "no live bacteria" in live commercials aired during the late night movie.
Why it's worth checking out: Sketchy businesses and late night local advertising are rich targets for parody, and you can’t get sketchier than a business that guarantees a $15 maximum price, has a former doctor (Martin Short) to testify about the mattresses “safety” (he’s also a customer), and identifies its target demographic as transients watching the commercial through a store window.
Worcester Centrum (David Alan Grier / Snoop Doggy Dogg, 01/18/1997)
What it's about: While monster trucks spin around in mud, funny cars build a civilization far more advanced than ours.
Why it's worth checking out: Likely only making it to air to fill time at the end of a show, this short commercial parody features stock footage, crude computer animation, and no castmembers whatsoever. It’s also one of the most bizarre, surrealistic concepts of the year, with the funny cars’ creating utopia, only for it to be destroyed by the jealous monster trucks (which the announcer compares to Visigoths), all within a Sunday event.
Chopper 4 (Chevy Chase / Live, 02/15/1997)
What it's about: Newsstand owner Andrew (Mark McKinney) is fixated on Chopper 4 and its ability to see through fog.
Why it's worth checking out: A very New York-centric piece with one of McKinney's more eccentric and less socially aware characters trapping Chevy Chase in conversation and a premise around local promotions for WNBC’s news helicopter (while not referenced by call letters, the “channel 5” and “channel 7” mentioned are the city’s Fox and ABC stations).
Job Interview (Jeff Goldblum / En Vogue, 05/17/1997)
What it's about: Oveconfident job interviewee Jerry "Steve" Dave (Tim Meadows) is laid-back, unprofessional and underqualified for an engineer position.
Why it's worth checking out: The combination of ineptitude and overconfidence is a reliable comedy formula, especially when it involves someone trying to parlay a few pottery courses and being "supergood" at things into an high-skill position; the character works because of Tim Meadows' likability and enthusiasm.
Buddy Songs (Brendan Fraser / Bjork, 10/18/1997)
What it's about: Brendan Fraser’s songs about his new buddy Will Ferrell creep out the entire cast, except for Norm Macdonald.
Why it's worth checking out: There’s something funny enough about Fraser singing innocent songs of friendship (and Ferrell resting his hand on his leg with a stupid grin), but Norm Macdonald being the one cheering them on with a big grin on his face is what really makes this sketch.
Cobras (John Goodman / Paula Cole, 02/07/1998)
What it's about: Pilot (Will Ferrell) calmly informs passengers on a Hawaii-bound flight that there are cobras loose on the plane.
Why it's worth checking out: Before Snakes On A Plane, this sketch had John Goodman, Ana Gasteyer and Tim Meadows terrorized by several snakes on what Ferrell eventually concedes is a “death flight”, before getting bit himself and describing the madness brought on by the cobra venom, all said in the same calm voice he uses for describing the altitude and view. Even weirder, the sketch ends with a monologue by a cobra puppet (voiced by Cheri Oteri), who gleefully talks of how it tricks unsuspecting people.
Loews (Garth Brooks, 02/28/1998)
What it's about: Moviegoers are trapped in an endless stretch of previews for bad movies, many of them starring Shelley Long.
Why it's worth checking out: One of the first sketches where the writers figured out what to do with Tracy Morgan, who plays the exuberant audience member that actually enjoys the previews. The offscreen terrible movie trailers are pretty funny in themselves too ("Shelley Long has just met the man of her dreams. The only problem? He's a puppet!")
Shirtless Bible Salesmen (Julianne Moore / Backstreet Boys, 03/14/1998)
What it's about: Leif Barrett (Will Ferrell) and Kent State (Tim Meadows) lack both shirts and sense when trying to sell bibles to a housewife (Julianne Moore).
Why it's worth checking out: This 10-to-1 sketch by Matt Piedmont is full of quotable lines (“This bible reeks of class!”) and absurdist non-sequiturs (“You see this watch? This is how much the Lord loves you”), and Ferrell and Meadows’s characters seem to operate according to the same logic that Jerry Steve Dave uses.
Jim Halsey's Truck Driving Museum (Steve Buscemi / Third Eye Blind, 04/04/1998)
What it's about: Jim Halsey (Will Ferrell) profiles the Kenworth RX-40TD with his assistant Wiley Lunt (Steve Buscemi)
Why it's worth checking out: This sketch doesn’t have any real jokes in the dialogue, just Ferrell talking about the specific features of a tractor-trailer made in the 1970s; the humor comes from the visual of Buscemi (who doesn’t say a word in this sketch) standing awkwardly and fidgeting during Ferrell’s spiel.
Shirt in a Can (Lucy Lawless / Elliott Smith, 10/17/1998)
What it's about: When you stain your shirt and don't have time to change, spray-paint a shirt right onto your own body.
Why it's worth checking out: Tim Meadows yelling “DAMMIT!” is one of the highlights, but this commercial parody is packed with fun little details (like the disclaimers about avoiding prolonged contact and how the product is not for use on genital areas), and the announcer waving off Meadows’ “IT’S BURNING MY SKIN!” with “that’s what tells you it’s a shirt!”
Accruing Equity and Making Hot, Sweet Love (David Spade / Eagle-Eye Cherry, 11/07/1998)
What it's about: Steamy stories of erotic encounters are mixed in with discussion of the day's financial news.
Why it's worth checking out: Will Ferrell and Ana Gasteyer’s ability to switch from straight-laced business news discussion to moans of ecstasy and back again is impressive, and David Spade gets laughs with his character’s weird and offputting story about an encounter in a Wendy’s.
You're A Champion, Charlie Brown (Brendan Fraser / Busta Rhymes & The Roots, 02/13/1999)
What it's about: Lucy's (Ana Gasteyer) "pulling the football away at the last minute" prank causes Charlie Brown (Brendan Fraser) to crack his skull open.
Why it's worth checking out: Besides the great visual of the cast with prosthetic round heads to look like the Peanuts gang, this has a lot of fun lines and references to the comic strip, including Lucy tearfully admitting that she wasn’t a doctor (“It was just a scam to make NICKELS!”) and the paramedics being represented with the muted trombone used for the adult “voices” in the cartoon specials.
Happy Smile Patrol (John Goodman / Tom Petty & The Heartbreakers, 04/10/1999)
What it's about: A kids show is interrupted by graphic news bulletins about the stars' kid-unfriendly personal lives.
Why it's worth checking out: The juxtaposition of pitch-black and lurid news bulletins during a saccharine-sweet show aimed at preschoolers and is well executed, particularly the clip of Cheri Oteri’s kid’s show character dancing in slow motion as the anchor (Chris Parnell) tells of the actress performing sex acts on a customs official before murdering him.
Dusty's Love (Sarah Michelle Gellar / Backstreet Boys, 05/15/1999)
What it's about: A TV matinee of a terrible movie from the 1970s about a blind girl (Sarah Michelle Gellar), her horse, and the monster (Horatio Sanz) who loves her, with music by Paul Williams (Will Ferrell)
Why it's worth checking out: This is one of the strangest sketches done in that period of the show, with the aforementioned random plot elements, the father (Chris Parnell) having dark hair and a red beard that grows long between scenes, a crude “humping scene edited for television” disclaimer card, and the translucent visages of Paul Williams and his “twin” backup singers superimposed over the scenes during the musical interludes.
Javis Home Security Systems (Jerry Seinfeld / David Bowie, 10/02/1999)
What it's about: Man (Will Ferrell) acting as if he were in a diaper commercial is actually the kind of weirdo that can intrude your home .
Why it's worth checking out: While many people complain about SNL sketches being overlong and belabored, this short fake-out blackout commercial parody ends at the right time.
WXLU (Garth Brooks / Chris Gaines, 11/13/1999)
What it's about: Executive (Tim Meadows) commissions a new opening title sequence to make the news team more likable, but it ends up being more appropriate for a kids’ show.
Why it's worth checking out: In addition to the news title sequence, which has Ana Gasteyer pretending to be an elephant and Tracy Morgan in a Mozart wig, there’s a lot of random humor in the scenes with the executives, particularly Will Ferrell trying to freeze frame, then slowly backing away.
Christmas Urchins (Jennifer Aniston / Sting, 11/20/1999)
What it's about: A family’s Christmas decorations includes actual rented street urchins (Jennifer Aniston and Rachel Dratch)
Why it's worth checking out: One of Rachel Dratch’s first notable sketches, with her and Aniston playing brothers who sing about the various diseases they have and offering to kill strangers in order to have a place to sleep.
Erectile Dysfunction (Julianna Margulies / DMX, 02/12/2000)
What it's about: A commercial shoot gets personal about the main actor's (Will Ferrell) erectile dysfunction.
Why it's worth checking out: Ferrell mostly plays it straight, at least until the humiliating story about a failed sexual encounter that causes him and his girlfriend (Julianna Margulies) to start sobbing (him in a high-pitched voice); most of the humor comes from his frustration and embarrassment, but the ending reveal of the product ID provides the biggest laugh of the sketch.
The Census (Christopher Walken / Christina Aguiliera, 04/08/2000)
What it's about: Mr. Leonard (Christopher Walken) has some unusual answers to the census-taker's (Tim Meadows) questions.
Why it's worth checking out: This sketch by Tina Fey aired in the same show that had “More Cowbell”; in my opinion this is the better sketch, with Walken’s trademark line delivery making the jokes even funnier, and Meadows giving one of his best straightman performances.