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.
Blind Date (Rob Lowe / Eminem, 10/07/2000)
What it's about: Rick (Will Ferrell) and Ray (Molly Shannon) have an excruciatingly awful blind date at an airport bar.
Why it's worth checking out: This is an oddity for an SNL sketch made in the last 25 years, with Will Ferrell and Molly Shannon both playing subdued in a scene centered more around awkward silences than clear jokes; a 1988 spoof of Friday Night Videos where Justine Bateman and George F. Will (Dana Carvey) mined similar territory, but this sketch doesn’t have as clear a premise. I wonder how this played at read-through or even at dress rehearsal; either way, it was a ballsy choice to have this sketch in the same night that gave the world “strategery” and the debut of the Fallon-Fey Weekend Update.
No Taint (Conan O'Brien / Don Henley, 03/10/2001)
What it's about: Ted Brown (Horatio Sanz) is despondent after learning he lost the area between his rectum and genitals in a car accident.
Why it's worth checking out: This sketch is crammed with ridiculous bits right from the outset, where Ted tells his wife (Rachel Dratch) he’s going to the “good McDonald’s” in another city instead of the one across the street. From there, it only gets stranger, from a doctor (Conan O’Brien) who can’t pronounce “Brown” to the wife remarrying a guy with a massive taint (Will Ferrell), as well as my particular favorite line in the sketch: “Where did you get your medical degree, in a box of Hill Street Blues cereal?”
Der Lacheln Beherrscht (Julia Stiles / Aerosmith, 03/17/2001)
What it's about: Nickelodeon presents the American debut of a terrifying kids’ show imported from Germany.
Why it's worth checking out: Any excuse to have Will Ferrell yelling in a German accent is a valid one, but this sketch was the perfect use for it, with a scary doctor (Horatio Sanz) serving “treats” of coffee and radishes, a skeleton dropping from the ceiling to sing “I’m Inside Every One Of You”, and lessons on how to behave at funerals.
The Flamingo Paradise Lounge (Pierce Brosnan / Destiny's Child, 05/05/2001)
What it's about: Frankie DeRosa (Horatio Sanz) emcees the only Las Vegas floor show that’s also a licensed daycare facility.
Why it's worth checking out: Sanz manages to pull off playing Las Vegas lounge singer and children’s entertainer simultaneously, and this also has some good work from Jerry Minor (as his accompanist), Tina Fey (as a dancer suggestively making balloon animals), and Maya Rudolph (as a dwarf announcing “snack time!”).
MSNBC Investigates (Lara Flynn Boyle / Bon Jovi, 05/12/2001)
What it's about: A teenage boy (Chris Kattan) is in a coma after injuring himself while he and his friends imitated The Golden Girls.
Why it's worth checking out: Airing nearly a decade before SNL booked Betty White, this sketch satirizing Jackass-related injuries via the pop-culture ubiquity of the 80s sitcom is even funnier all these years later.
Little Sleuths (John Goodman / Ja Rule, 11/03/2001)
What it's about: 12-year-old amateur detective Bookie Newton (Seth Meyers) and his kid sister Sam (Amy Poehler) help solve the case of a murdered prostitute.
Why it's worth checking out: Five years before anchoring Weekend Update together, Amy Poehler and Seth Meyers co-wrote this sketch that only made it to air once in the 10-to-1 slot'; It may not have been the hit recurring sketch its creators hoped it would be, but it was the start of a very fruitful on-screen partnership.
War Party (Billy Bob Thornton / Creed, 11/17/2001)
What it's about: News of the fall of Kandahar prompts party-goers to do a campy 60’s style song-and-dance number.
Why it's worth checking out: This is a snapshot of a specific time, that period between the 9/11 attacks and the start of the Iraq war; this is also a random as hell sketch, with choreography by Danielle Flora (who also appears in the sketch) and the cast nonsensical lyrics about going skinny-dipping and having a date in Kandahar before Tracy Morgan enters to give a dramatic monologue.
Music International (Jack Black / The Strokes, 01/19/2002)
What it's about: Songwriter (Jack Black) performs his new heavy metal-style replacement for the “Happy Birthday” song.
Why it's worth checking out: Will Ferrell’s entrance wearing a bad 70’s wig to ask “Does this look familiar” would almost steal the whole sketch if not for the elaborate number that follows, which is supposed to replace the “difficult to remember” and “hard to sing” version.
Hot Air Balloon Mystery Theatre (Sir Ian McKellen / Kylie Minogue, 03/16/2002)
What it's about: Professor (Ian McKellen) solves the murder of a judge (Chris Kattan) that happened aboard a hot air balloon ride.
Why it's worth checking out: This is goofy fun, with the cast doing their best (worst?) upper class English accents, McKellen chasing the murderer (Chris Parnell) around the cramped space of the balloon basket, and Kattan lying lifelessly over the edge.
White Men Black Women (Alec Baldwin / P.O.D., 04/20/2002)
What it's about: Tom’s (Alec Baldwin) friends are upset that he and other middle-aged white guys are dumping their wives for elderly black women as soon as they make it.
Why it's worth checking out: This sketch, taking a race-and-age-reversed version of successful black men leaving their wives for younger white women to extremes, is a little questionable in execution, but has Tracy Morgan, Maya Rudolph and Dean Edwards playing grandmother types (particularly Morgan excitedly talking about going on a date to church and Edwards playing his character with a Caribbean accent)..
Be Safe Gang (Sarah Michelle Gellar / Faith Hill, 10/12/2002)
What it's about: Cops (Fred Armisen, Sarah Michelle Gellar, Amy Poehler) give safety tips in a classroom presentation that are questionable at best.
Why it's worth checking out: One of Armisen’s earliest SNL sketches has him giving useless strategies in dealing with muggers (pretend to be talking on the phone and they’ll go away), and his partners suggesting condoms lead to “crotch botulism”. At a time when the show was reeling from the departure Will Ferrell, Armisen and fellow new addition Will Forte were responsible for some of the highlights of this very uneven season.
Game Night (Eric McCormack / Jay-Z, 11/02/2002)
What it's about: A game of “Celebrity” brings out a competitive and violent side in a party guest (Rachel Dratch).
Why it's worth checking out: Dratch’s rampage at the end (“WHO THE BALLS WROTE FELIX MENDELSSOHN?”); this also fakes out somewhat by making the audience think the comedic hook is Eric McCormack’s incompetence at the game, but the focus slowly pivots to Dratch over the course of the sketch.
Give Up The Ham (Queen Latifah / Ms. Dynamite, 03/08/2003)
What it's about: When a fight over a ham pits race and class against each other, butcher (Will Forte) sings a plea for unity.
Why it's worth checking out: Queen Latifah (only the third black woman to host SNL), and Amy Poehler playing two women fighting over a ham in a grocery store is a simple enough premise, but this builds to include Maya Rudolph, Rachel Dratch, and a crossdressed Tracy Morgan and Chris Kattan before Forte comes out to sing a 60s style song as Chris Parnell explains this sketch largely came about from a writer drinking a case of Rheingold Beer. The slow escalation into absurdity and silliness makes this a keeper.
Box (Salma Hayak / Christina Aguilera, 03/15/2003)
What it's about: Ray (Will Forte) mails himself in a giant box to catch his cheating wife (Salma Hayak) in the act, but can’t do much about it while inside.
Why it's worth checking out: A good example of the “weird Forte sketch” that ended up being a highlight of the show’s post-Will Ferrell, pre-Andy Samberg awkward years. Forte only punches his arm out (and later smushes his head through the opening), but gets a lot of laughs while constrained inside the box, whether it’s slowly hopping it to the other side of the room or egging Jimmy Fallon on to beating up on the giant package.
Phone Booth (Ray Romano / Zwan, 04/12/2003)
What it's about: A sadistic sniper (voice of Darrell Hammond) torments Walter (Ray Romano) by forcing him to embarrass himself.
Why it's worth checking out: A spoof of the then-current Colin Farrell movie, this stands alone as its own sketch, with Romano being forced to admit his penis size, sleepwear preferences and make a racist statement to a black cop (Tracy Morgan, who gets laughs of his own from his responses).
Speed Reader (Halle Berry / Britney Spears, 10/18/2003)
What it's about: Gary (Will Forte) is confident that his ability to read books in seconds will help him bed Jasmine (Halle Berry)
Why it's worth checking out: Another “weird Forte sketch”, this one came at the end of a particularly weak show, and also seems to be Forte and Berry racing against the clock to get their lines in before the show goes to its last commercial. It’s also got Forte’s ability to play cocky endearingly, and the scene where he speed-reads the Bible (“DONE! Pooooor Jesus.”)
Mike's Bar (Drew Barrymore / Kelis, 02/14/2004)
What it's about: In 1968, soldier on leave John Kerry (Seth Meyers) meets recent Yale grad George W. Bush (Will Forte) and future law student Bill Clinton (Darrell Hammond) in a New Haven bar.
Why it's worth checking out: Will Forte took over the George W. Bush impression from Darrell Hammond beginning with this sketch, which was a more interesting way to handle the political material in a year of fairly uninspiring Democratic challengers (Meyers plays Kerry as a too-serious stick-in-the-mud). The current writers, who seem a little too content with having Alec Baldwin re-enact the week’s news items, need to take lessons from this sketch.
Firing Sandy (Christina Aguilera / Maroon 5, 02/21/2004)
What it's about: Mr. Williams (Chris Parnell) tells rude and frequently absent employee Sandy (Will Forte) he’s being let go.
Why it's worth checking out: As funny as Forte is, this scene wouldn’t be as great without Chris Parnell in the straight role to provide a contrast of normalcy against the shamelessly lazy Sandy; even when Forte takes his character to more ridiculous levels of belligerence, Parnell keeps the scene tethered to the real world.
Jesus: Hollywood vs. History (Colin Firth / Norah Jones, 03/06/2004)
What it's about: Liam Neeson (Colin Firth) presents Benny Hill’s (Will Forte) controversial unreleased Biblical epic “J.C. Godson & Co.”
Why it's worth checking out: You know what it’s leading up to once Neeson mentions Benny Hill, but the sight of Forte dressed as Hill chasing bikini-clad girls to “Yakety Sax” while tied to a crucifix always brings a smile..
Good Times (Janet Jackson, 04/10/2004)
What it's about: Florida Evans (Kenan Thompson), her family, friends and neighbors all endure one tragedy and misfortune after another.
Why it's worth checking out: Thompson nails his Esther Rolle impression and it was an unexpected treat to have Janet Jackson reprise her role 25 years after the show ended, but this is also interesting for the fact that the show had enough black performers to do a parody of the 70s sitcom (though they cheat somewhat by having Maya Rudolph do double-duty as Thelma and Willona, Tracy Morgan in a cameo as Bookman, and writer J.B. Smoove playing J.J.)
The Adventures of Peter O'Toole and Michael Caine (Jude Law / Ashlee Simpson, 10/23/2004)
What it's about: Sozzled septuagenarian stars of stage and screen O’Toole (Jude Law) and Caine (Seth Meyers) stumble into a Taco Bell-Pizza Hut Express and think they’re hosting a talk show and acting workshop.
Why it's worth checking out: The nonsense that O’Toole and Caine spew is funny (I always remember the order for a “gin lovers pizza”), but this also has an early example of how Kenan Thompson adds to sketches by playing straight (and, well, reacting) against the craziness around him.
Drug Sniffing Dog (Liam Neeson / Modest Mouse, 11/13/2004)
What it's about: Stoners (Liam Neeson and Amy Poehler) try to borrow a drug-sniffing dog from the police station to locate their misplaced weed stash.
Why it's worth checking out: Another fairly simple premise, with Parnell once again playing the real-world authority figure who doesn’t buy the obviously fake stories Neeson is feeding him, and a funny ending involving Kenan Thompson.
Key Party (Colin Farrell / Scissor Sisters, 12/11/2004)
What it's about: Carol (Horatio Sanz) and husband Owen (Colin Farrell) are part of a motley crew of swingers that introduce themselves and their safewords.
Why it's worth checking out: Despite Sanz’s Carol being spun off into a lesser series of recurring sketches, this one-off that introduced the character works better, largely because Sanz’s over-the-top performance fits in better as one of a group of different eccentrics. This sketch also gets a lot of mileage from very little information and repetition: six of the ten swingers only say their names and safewords, but their outfit, delivery, names and safeword choices raise unanswered questions: Why does Leslie (Chris Parnell) change the pronunciation of his name and “filibuster? What’s the deal with Jean-Georges Peppers (Will Forte)?
Public Speaking Class (Jason Bateman / Kelly Clarkson, 02/12/2005)
What it's about: Students, including militaristic Bill (Rob Riggle), anxious Ann (Maya Rudolph) and gesture-dyslexic Simon (Chris Parnell) give their sales presentations.
Why it's worth checking out: A lot of SNL seems to be focused on one or two characters doing a specific thing and everyone else reacting to them, so scenes where different cast members each get their own unique bit to perform are good opportunities for them to play different types of characters. There are some good performances in here, but Parnell’s character has an impressive run of wildly inappropriate body language during his presentation.
Pepper Grinder (Will Ferrell / Queens of the Stone Age, 05/14/2005)
What it's about: When a waiter (Will Ferrell) tells a customer who turns out to be a family friend (Will Forte) he’s thinking of dropping out of Stanford, he gets a lesson in endurance from his mentor via the restaurant’s “complimentary pepper until the customer says when” policy.
Why it's worth checking out: Forte and Ferrell are two of SNL’s most intense, go-for-broke performers of all time, and while this sketch doesn’t have a ridiculous concept like either of their best work, this still gives both performers a chance to go head-to-head and try to outdo each other.