By Shirley Li
Updated October 02, 2015 at 07:36 PM EDT
Credit: Dana Edelson/NBC/NBCU Photo Bank via Getty Images

With Taran Killam set to play Donald Trump on Saturday Night Live this season, it’s time to revisit the show’s previous jabs at the hotel-magnate-turned-presidential-hopeful. From Phil Hartman’s early impressions to Darrell Hammond’s hilariously ludicrous caricature of The Apprentice personality to the Trumpster himself hosting the show in 2004, here are the eight most memorable (and one throwback) SNL takes on Donald Trump:

1. Ross Perot Interviews Pat Buchanan and Donald Trump (October 2, 1999)

Remember when American politics didn’t boil down to two parties? In 1999, Ross Perot’s moderate Reform Party was struggling to find a leader, and in this cold opening, Donald Trump is one of his replacements. With Cheri Oteri as Perot, Chris Parnell as a squinty Pat Buchanan, and Darrell Hammond as a pouty Donald Trump (in the first of many sketches), this Trump appearance kept the jokes coming, as Trump’s total lack of self-awareness leads to a proposal to turn the White House into a deluxe casino. Plus, this Trump defended keeping immigrants within the U.S. … sort of. “Sure, they steal and talk funny,” Hammond-as-Trump says, “but if they’re fresh off the burrito boat, they’ll work for 15 cents a week. I’ve seen it myself!” Oof.

2. Donald Trump Has Ideas for the Network (January 10, 2004)

By the time this cold opening ran, Hammond had nailed the signature nasally, monotonous voice and pout he would use for all of his Trump impressions. (And there would be many more to come, once The Apprentice became a downright hit for the peacock.) And though Jimmy Fallon stepped in for a short bit in the open as then-NBC Entertainment president Jeff Zucker, Hammond owned the sketch, delivering both absurd statements (“I just learned yesterday that my own Taj Mahal in Atlantic City wasn’t the first Taj Mahal”) and pompous lines (“If you’re a man, you want my life; if you’re a woman, well, I got what you want, okay?”) without breaking. Live from New York, it’s Donald Trump! Okay?

3. The Apprentice Halloween Promo (October 23, 2004)

And thus began a string of sketches with Hammond playing Trump doing an ad. It’s easy to see why: The control-freak nature of The Apprentice host was perfect for the sketch (“That was great,” he says at one point to himself after a take), as SNL gets to put the business mogul in crazy costumes and promote the network’s highest-rated show. (As Trump liked to remind his viewers.) Killing two birds with one stone? Trump would approve.

4. The New Trump Family (February 5, 2005)

Aside from The Apprentice and Hammond’s perfect delivery of the “You’re fired”(™) catchphrase, SNL had plenty of fodder to work with when it came to Trump’s home life. During the mid-2000s, both Paris Hilton and Trump’s marriage to Melania were — to borrow from Ms. Hilton’s vocabulary — “hot,” and SNL couldn’t resist having Maya Rudolph, Fred Armisen, and Seth Meyers play off of Hammond’s popular impression. The sketch may seem a bit “Californians“-like now with the exaggerated accents, but at the time, it played off of Trump’s mannerisms in the kookiest way.

5. Donald Trump Stars in a Domino’s Ad (May 7, 2005)

Just as he did in the Halloween plug for The Apprentice, Hammond-as-Trump refused to do exactly as he was told, especially when it came to pronouncing the name of the pizza restaurant for which he was shilling. Hammond topped his voice and pout by butchering words, a trait that would lead to …

6. Trump’s Cameo on Days of Our Lives (October 29, 2005)

This sketch saw Hammond’s impression of Trump hit overdrive, as he fails to say the name, “Arianne,” attempts an impression of The Godfather, and plays full doofus as he sticks a pipe in his mouth and claims he’s Sherlock Holmes. The sketch left the audience guffawing with every ridiculous take, and the cobbled together scene of his “cameo” on the soap served as a perfect kicker.

7. Monologue: Donald Trump and His Replacement (April 3, 2004)

Hammond’s fan-favorite impressions of Trump eventually nabbed the real Trump a chance to host the show, and in 2004, he brought out Hammond (as Trump, naturally), introducing him as a replacement the network could use in case he got tied up in his countless other responsibilities. This appearance, from more than a decade ago, got the crowd cheering, and Trump didn’t even blink as he took the support in stride. “I’ll be honest, it’s even bigger for Saturday Night Live that I’m here,” he says. “Nobody’s bigger than me.” Fallon even returned to play Zucker, and Trump had Hammon “fire” him over and over, saying he liked the way it sounded.

8. Live with Regis and Kelly: Donald Trump (April 3, 2004)

During the same show, SNL aired a sketch in which Trump played himself, and his SNL counterpart played an overly emphatic Regis Philbin (opposite an overly touchy-feely Amy Poehler as Kelly Ripa). The sketch was huuuge, thanks to Trump, well, saying so and to Hammond and Poehler gamely playing along with his bits plugging his book, How to Get Rich.

Honorable Mention: A Trump Christmas (December 10, 1988)

In SNL‘s first Trumptastic sketch, Phil Hartman played Trump and turned in a non-pouty performance that instead jabbed at the Trumps’ (Trump and his then-wife Ivana, played by Jan Hooks) excessive boredom over their own wealth. Watch for a throwback to the style of the late ’80s, as well as a clever twist involving the pair’s gold-plated gifts to each other.

Saturday Night Live returns this week at 11:30 p.m. ET on NBC.

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Saturday Night Live

The original late-night comedy sketch show from the one and only Lorne Michaels.

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