Alec Baldwin’s 10 Best Saturday Night Live Moments

This Saturday, Alec Baldwin kicks Saturday Night Live’s 42nd season off with a ripe parody target: Donald Trump, another broad-shouldered New Yorker who also doesn’t mince words.

Every time SNL’s host with the most (16 Baldwin-hosted episodes to date) drops in, the guy’s a total pro. The thing that makes the Baldwin effect reliably funny isn’t just his self-assured stature: he’s an experimental team player, and everyone around him is funnier for it.

Whenever he takes his homecoming king crown back, he reminds fans why the show loves him. Now, as we get ready for Baldwin’s Trump to spar with the excellent Kate McKinnon as Clinton, relive his greatest comedy moments with his 10 best Saturday Night Live sketches.

Watch The Tony Bennett Show: with the Real Tony Bennett
This season, searing headlines about the presidential candidate will likely power Baldwin’s SNL bits, but one of his most memorable and popular characters will always be the legendary singer. When he riffs about his old friends all jazzy like, it’s a great great great moment, every time.

Weekend Update: Steve Rogers on Alec Baldwin
If you thought Baldwin’s casting was at all meta, how about when he poked fun of his own news story: getting kicked off a plane for playing Words With Friends, or “a word game for smart people,” as he put it. SNL has given celebrities the stage to mine their controversy baths for laughs before with a non-apology, but this takes the cake. Seth Meyers is all “and another intense thing you reportedly did,” and Baldwin as the pilot who booted him is all “that Alec, what a national treasure!” He has never been more joyful than here when he’s luxuriating in his own drama.

Schweddy Balls
In an episode on the funniest desserts ever to touch an NPR host’s lips, this sketch needs no introduction. Screw The Cooler. Everyone knows Baldwin’s most important role was the bakery owner of Season’s Eatings, Pete Schweddy. If Baldwin has to say balls 80 times, he will do that with the straight face of a food podcaster no matter how funny Ana Gasteyer and Molly Shannon get. He will make you believe that he thinks his pride and joy—balls made of popcorn—are delightful things to behold. Correct you are, Baldwin, no one can resist your balled rum.

Brenda the Waitress
The underlying motives in this slow-paced sketch with fast-paced dialogue lead by Jan Hooks and the 30 Rock actor supplied the show with one its the most rock solid moments ever. Without a silly setup, an oddball character flaw or a big news story to play with, this scene ran on a ton of innuendo, and they both knocked it out of the park.

The SNL Platinum Lounge
Ladies and gentlemen, let the show present the most well-crafted Martin and Baldwin sketch ever. Sometimes when they pair these two up at the last minute, it’s undercooked and it shows. But not at the platinum lounge where the show’s fun with their rivalry hit a high point, thanks to sneaky Steve. Martin trying to poison Baldwin out of his world record title worked incredibly well. This was New York-centric, purposefully old school and perfectly cheesy.

Glengarry Christmas: Elf Motivation
A common premise: whipping Santa’s workshop into productivity shape, this time, Glengarry Glen Ross-style. Tough-talking Baldwin plays a few of his roles form his IMDB page: Glengarry Glen Ross, The Departed and his role in life itself, but he gets a hat with a bell on it. It’s the story only Baldwin can tell: No one can call a bunch of people “losers” with a face as stern as his.

Canteen Boy
About a creepily persistent boy scoutmaster putting the moves on the 27-year-old boy scout, “canteen boy” (Adam Sandler), this classic is unforgettable for good reason. Non-stop laughter ensues as the debonair camp counselor encroaches further and further into the less and less oblivious camper’s personal space. The comedy worked on several levels, most hilarious of all Sandler’s quivering lips as he reacts to those unwanted moves with all the camp survival jokes.

Bill Brasky Airport Bar
Baldwin was a (rare) ensemble player in this SNL classic in which salesman swap war stories about a legendary fake person, Bill Brasky. Baldwin, it may surprise you, is totally, commendably unrecognizable as he recounts that time Brasky pulled the ultimate Brasky: baptism by scotch. Some superb voice acting, plus his ability to arrange his face into this expression will certainly prove itself handy with the Donald.

Monologue: Alec Baldwin Learns the True Meaning of Hosting SNL
His Charles Nelson Reilly might be funnier, but it’s also worth noting his pathos in this monologue from his eighth round as host. In it, he goes through a Christmas Carol-style tour of a Baldwin-less episode. He manages to recreate those redemption vibes despite the absurdity, and as always he comes through. Don’t discount heartwarming Baldwin. (Special note: Jimmy Fallon predicts he will host the show in 2011, and he does.)

The Joe Pesci Show: Robert DeNiro, Mel Gibson, Danny Glover and Brad Pitt
Here, on the disappointingly non-existent The Joe Pesci Show, our new Trump impressionist engages in one of his time-honored power moves on the show, slipping people cash with a smart impression. He makes for an understated, but convincing DeNiro, and you can feel his reverence for the actor. Still a crowd favorite.