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Fact #1: Jay Leno has been the most popular late night host in America for the majority of the past 19 years.

Fact #2: Comedians, Hollywood insiders, and laypeople alike just love hating on Leno, and have been doing so consistently for over 20 years.

Why? In their minds, the reasons are legion: Because he stole The Tonight Show from Johnny Carson’s rightful heir, David Letterman, way back in the early ’90s. Because he refused to simply retire when NBC tried to replace him with Conan O’Brien in 2009. Because his primetime Jay Leno Show tanked, sinking Conan’s Tonight Show before it had even really begun — and eventually forcing Conan to leave NBC for good. And most of all, because they say his jokes are broad, pandering, and eminently unfunny — which is a shame particularly because once upon a time, Leno had a reputation for being one of standup’s sharpest and edgiest comedians.

So as Leno prepares for his final few Tonight Shows, he finds himself in a unique position: More widely watched than any of his competitors, yet widely reviled by the majority of his peers. How widely, you ask? Let’s take a look back at the most notable jabs, slights, and straight-up insults famous people have aimed at Leno over the years — starting shortly after NBC revealed that he, rather than Letterman, would become Tonight‘s next host. (Insert “Jay takes it on the chin” joke here.)

Spring 1992

Leno is set to inherit The Tonight Show from Johnny Carson in May. Before the big premiere, he chats about his career in a 60 Minutes segment that also includes agent Helen Kushnick recalling all the rejection Leno faced in his early years — “He was too dark, he was too ethnic, he was too menacing — they actually did tell me that they thought he’d be frightening to children” — and his wife Mavis remembering a casting director who spurned her husband, then put out a notice for a “good-looking Jay Leno.”

April 17, 1992

Upstart host Arsenio Hall comes gunning for Leno in an EW cover story: “I always hear that Jay and I are friends when they interview him,” he says. “Jay and I are not friends…I have no problem about saying good things about my competitors, but Jay Leno and I aren’t friends! And you know what? I wasn’t anointed, okay? No one put the late-night silver spoon in my mouth. I earned every drop of mine. And I’m gonna treat him like we treated the kid on the high school basketball team who was the coach’s son. He was there because he was anointed too. We tried to kick his ass, and that’s what I’m going to do — kick Jay’s ass.”

May 22, 1992

Johnny Carson hosts his last Tonight Show ever. Leno neither appears nor merits a mention.

August 1992

Carson’s ex-bandleader Doc Severinsen takes a shot at Leno, who began hosting Tonight May 25. The show’s new team is “a bunch of screwballs,” he tells USA Today. “Jay Leno is running around trying to figure out ‘How can I get them to like me?’ Frankly, I haven’t seen anything that makes me want to stay tuned in.”

October 7, 1992

Ed McMahon does a guest spot on Arsenio Hall, praising the work of Leno’s rival and giving him a replica of the cup McMahon used on Tonight — an indirect Leno dis, but a dis all the same.

July 17, 1992

Arsenio Hall talks on air about the recent cancellation of The Dennis Miller Show. Of course, he thinks the wrong guy is getting kicked off the air: “He should be staying, and that punk-ass Leno should be going.”

July 20, 1992

In an interview with Good Morning America taped today, Hall explains that his Leno beef is “personal”: “Jay and I used to be friends,” says Hall. ”Dennis [Miller] and Jay used to be friends… Something’s wrong with someone who is always surprised about people being upset with him.”

Also: Miller addresses his show’s cancellation on air. “I feel like Ross Perot,” he jokes, before announcing that he’ll “release all my delegates to Arsenio Hall and David Letterman.” Guess whose name Miller didn’t say?

August 14, 1992

So, how does Miller really feel about Leno? ”Jay and I were very good friends at one point,” the comedian tells EW in a cool tone. ”I don’t think I’d talk to him again, nor would he want to talk to me. About The Tonight Show, put it this way: They want to win really badly.”

Sept. 4, 1992

In the pages of EW, Arsenio slams the magazine for drumming up the feud between him and Leno… while simultaneously slamming Leno for allegedly spreading a “racist and insulting” rumor about him. Hall also notes that he managed to coexist “with Mr. Carson and Mr. Letterman for more than three years without any of us saying a negative thing about the other.”

Oct. 18, 1992

Jim Carrey debuts his Leno impression on In Living Color: a squealing preener who promises a “similar” show to last night’s in his monologue and can’t control his bandleader, his guest (Sinead O’Connor, fresh off her SNL performance), or his audience, all of whom eventually defect for Arsenio. Man, this clip is such a time capsule.

October 7, 1993

In his memoir Private Parts, Howard Stern recalls being incensed about McMahon and Severinson’s actions the previous year, calling them “underhanded attack[s] on nice Jay.” Stern then quotes something he said on his own radio show: “How can you be pissed at Jay Leno? He’s like a puppy. There couldn’t be a better asskisser in the U.S. than Jay Leno.” And remember, that’s Stern defending Jay.

February 22, 1994

Hyperion publishes The Late Shift, Bill Carter’s in-depth account of Leno and Letterman’s battle over The Tonight Show. Among its revelations: At one point, Leno hid in a closet to eavesdrop on a conference call between NBC executives. Throughout the book, Letterman is painted as a surly comic genius, while Leno is both an overly eager people pleaser and a two-faced machine willing to do whatever it takes to win. Neither comes out smelling like a rose, but the book concludes that NBC made an error in judgment by choosing Leno over Letterman.

May 13, 1994

Carson appears briefly on Letterman’s Late Show, though he’s never appeared on Leno’s Tonight Show. And he never will: the Letterman cameo turns out to be Carson’s last TV appearance period.

June 22, 1994

“We got a great show tonight!” an animated Leno announces on an episode of The Critic. “Our guests are… the same guests Letterman had last night! And you’ll really enjoy the chemistry between Branford and me!” Cut to Tonight bandleader Branford Marsalis: “Shut up, man.” Oh, and fun fact — Leno’s voice is performed by a young Judd Apatow.

February 25, 1995

While hosting SNL, George Clooney plays Leno as a genial psychopath in a Taxicab Confessions sketch. (Cabdriver: “Jay, did you ever kill anybody?” Leno: “Yeah. I I pushed a guy in front of a subway once. Good guy, though.”) The chin, naturally, is out of control.

February 23, 1996

Late Shift: The Movie premieres on HBO, starring Daniel Roebuck’s Leno — a simpering Mike Tyson soundalike with an enormous prosthetic jaw.

May 28, 1998

Clay versions of Leno and Letterman fight to the finish on MTV’s Celebrity Deathmatch. The show depicts both as pandering hacks who host “almost unwatchable” shows, and in the end they’re each crushed by the crisp corpse of the Loch Ness Monster (don’t ask). But naturally, there are also jokes about Leno’s chin and his high voice.

March 1, 2000

Letterman has spent years studiously ignoring Leno. Tonight, though — shortly after a heart surgery that’s left him looser and more daring than he’s been in years — he breaks his silence, mocking Leno’s recent interview with George W. Bush: ”Now, there‘s a real summit meeting,” Dave scoffs. Then he does the high-pitched Leno impression that will eventually become something of a signature.

March 3, 2000

Meet Johnny Rotten, who despises both Letterman and Leno: “I hold both of them in nothing but the most complete and utter contempt,” he tells EW. “If they were two sides of a coin, I’d toss it in the river.”

Fall 2002

Months before his new ABC late night series is set to premiere, Jimmy Kimmel ruffles Leno’s feathers by telling TV Guide that he plans to do “the comedy version of the Tonight show.” A hurt Leno reportedly calls Kimmel for an explanation, and the two patch things up… for now.

November 3, 2002

Late Shift author Bill Carter brings up Kimmel’s quip in a New York Times interview — and Kimmel doubles down, saying, “Leno was so great when he was a guest on Letterman…I just think he’s worked it too hard. I think he turned comedy into factory work — and it comes across.” He also says that Leno called his publicist after reading the “comedy version” quip, adding, ”It’s just amazing how insecure he is.” And finally, the kicker: “The people who like Leno are largely the stupid group. The people who root for Letterman are the smarter group. The people who like me? Also stupid. I figure I cut into the dummies.”

January 19, 2005

Days before Johnny Carson’s death, word breaks that the King of Late Night still sends Letterman monologue jokes — and that Letterman occasionally uses them. Leno, of course, continues to go unmentioned.

September 18, 2005

The Emmys present a touching tribute to the late Carson. The segment is anchored by Letterman; Leno appears neither in its clip montage nor onstage. In fact, his name isn’t so much as mentioned in the tribute — and a Tonight Show publicist tells EW that Leno wasn’t even asked to participate in it.

January 24, 2007

In a radio interview, George Lopez calls Leno “the biggest two-faced dude in TV,” adding that he’s also a backstabber and “the worst interviewer on TV.”

April 14, 2009

GQ asks Leno if it’s true that he wrote Letterman a note after Dave’s open-heart surgery. Leno says it’s true, that he wrote about “just how funny I thought he was and how I owed him a lot, how important he was to me and all that…” and that Letterman never responded. Ouch.

May 19, 2009

Word has broken that instead of retiring fully at the end of the season, Leno will cede Tonight to Conan O’Brien while starring in his own nightly primetime comedy show. At ABC’s Upfront presentation, presenter Jimmy Kimmel jokes that NBC is so desperate to keep Leno from jumping ship that it’s willing to “destroy the network” in the process.

June 8, 2009

Howard Stern predictably rips on Leno’s last Tonight show as host (for now): “I’ve never seen anybody who behaves like a robot like this guy. Where’s the emotion? Where’s the humanity?”

June 9, 2009

Dave loyalist Julia Roberts on Letterman: “You are so much funnier than other people who talk at this time of the evening.” Sure, by now Jay has moved to his doomed 10 p.m. time slot— but somehow we don’t think she’s referring simply to Mr. O’Brien.

November 1, 2009

In a lengthy, candid interview with Broadcasting & Cable — which also features Leno admitting that he’d rather still be hosting Tonight than The Jay Leno Show — Jay recalls his “favorite” insult from the press: “Someone on a blog said they hope I die of AIDS in one of my old cars.”

January 7, 2010

Word breaks that NBC wants to reduce Jay Leno to 30 minutes and push it to 11:35. This would mean giving Conan’s show a new start time of 12:05 a.m. — moving Tonight to tomorrow and effectively forcing O’Brien to play second fiddle to Leno once more. The news… does not go over well.

January 8, 2010

Patton Oswalt weighs in on the brewing controversy, comparing Leno’s rise and “drive to power” to that of Richard Nixon and calling Leno a passive-aggressive fake who’s grown content with mediocrity: “Comedians that don’t like Jay Leno now, and I’m one of them — we’re not like, ‘Oh my God, Jay Leno sucks.’ It’s that we’re so hurt and disappointed that one of the best comedians of our generation willfully, like, threw that switch off .”

January 11, 2010

Letterman gleefully tears into the NBC situation, repeatedly calling Leno “Big Jaw” and performing his squealing Jay impression. For now, he also keeps things relatively self-deprecating; he opens his monologue by saying wryly, “Well, once again, I did not get The Tonight Show.”

Also, Stephen Colbert has Morgan Freeman, “the most trusted voice in America,” read a list of untrustworthy things — including this line: “Conan! The 11:30 slot — yours.”

January 12, 2010

Letterman doubles down on Leno, proposing a Law & Order spinoff called Leno Victims Unit — which will tell stories of the “two kinds of talk show hosts: Jay Leno, and those who have been victimized by Jay Leno.”

But this can’t hold a candle to Jimmy Kimmel, who spends an entire episode of Live performing a cruel impersonation of Leno — complete with a floppy gray wig and an enormous prosthetic chin. Here’s how his monologue begins: “Hello! My name is Jay Leno. You might have known, I’m taking over all of the shows in late night. Even this one. Great to be here on ABC. You know what ABC stands for? Always Bump Conan. That’s right. Anyway, Conan O’Brien today announced he’s leaving NBC. He released a statement that said, ‘I won’t participate in the destruction of the Tonight Show.’ Fortunately, though, I will.”

January 13, 2010

Letterman: “Last night on ABC, Jimmy Kimmel did the entire show as Jay Leno. Jimmy Kimmel was so convincing as Jay Leno, they canceled him.”

January 14, 2010

Leno responds to Kimmel’s impersonation episode by inviting the younger host to do a satellite interview on Jay Leno. He instantly regrets that decision once Kimmel starts answering his questions:

Leno: What’s the best prank you ever pulled?

Kimmel: Well, when my Aunt Chippie was at work, I painted her house orange and green one time… But I think the best prank I ever pulled was, I told a guy that five years from now I’m gonna give you my show and then when the five years came, I gave it to him and then I took it back almost instantly. It was hilarious…I think he works at Fox or something now.

Leno: Ever ordered anything off the TV?

Kimmel: Like NBC ordered your show off the TV?

Leno: Is there anything that you haven’t hosted that you want to host?

Kimmel: [pause] Oh, this is a trick, right? Where you get me to host The Tonight Show and then take it back from me?

Kimmel will later call the segment his proudest moment; Leno will later describe the jabs as a “sucker punch.” The two haven’t spoken since, at least as of a 2013 Rolling Stone interview.

Meanwhile, Conan’s Tonight monologue includes this blistering line: “Hosting The Tonight Show has been the fulfillment of a lifelong dream for me, and I just want to say to the kids out there watching, you can do anything you want in life. Unless Jay Leno wants to do it too.”

January 18, 2010

Letterman again: ““I’m telling jokes and making fun of Jay Leno relentlessly, mercilessly, simply for one reason: I’m really enjoying it. It’s just fun!”

Feb. 7, 2010

Mere weeks after Conan hosts his last Tonight Show, CBS presents a Super Bowl commercial for the ages that unites Letterman, onetime Letterman hater Oprah Winfrey, and Leno. The ad reportedly marks the first time Leno and Letterman have interacted in 18 years — and though the mood on set was professional and cordial, Leno still ends up the butt of the joke.

March 2, 2010

The day after Jay officially returns to Tonight, Howard Stern tells CBS Early Show host Harry Smith that Leno “makes [him] want to vomit.”

May 6, 2010

Craig Ferguson cracks a monologue joke that bombs, then refers to the quip as a “Leno joke” and follows it with a goofy impression of Jay.

April 6, 2010

Why are there so few close-ups of Slash while he’s performing on Leno’s Tonight? Simple: Because the guitarist is wearing an “I’m With Coco” pin on his lapel.

June 8, 2010

Tonight Show with Jay Leno guest Chris Rock opens his interview by alluding to the Conan controversy: “Last time I was here, you weren’t here. Some redhead guy said you’d be right back,” he says jovially. Later, Rock interrupts Leno, saying, “I can’t believe you’re back! You’re a bad man, Jay Leno.” Perhaps uncoincidentally, Rock hasn’t appeared on Leno’s Tonight since.

November 4, 2010

Bill Carter publishes a follow-up to The Late Shift called The War for Late Night: When Leno Went Early and Television Went Crazy. Once again, he emphasizes Leno’s insane work ethic — Jay doesn’t even understand the idea of vacations — and obsessive desire to be loved. In the end, Leno comes across as pathetic and desperate: He’s devoted his entire life to his work, and he doesn’t know what to do when faced with the possibility of his show being taken away.

November 9, 2010

Letterman notes that Hillary Clinton has denied that she’ll run for President in 2012. But “is she really not running,” he asks — “or is she just pulling a Leno?”

January 18, 2011

Howard Stern tells Piers Morgan that Leno is “insane” and “a crook” who’s “not fit to scrub David Letterman’s feet.” Also, he doesn’t like Jay personally. Who’da thunk?

May 4, 2011

In “Funnybot,” South Park includes Leno among the hacks who are furious when Jimmy’s comedy robot puts them out of work. At one point, an enraged Jay threatens to kill everyone in South Park Elementary’s gym.

December 13, 2011

In the DVD cut of the Family Guy episode “And Then There Were Fewer,” we learn that elderly, limbless pirate Seamus and unrepentant pedophile Herbert prefer Leno to Letterman. “I’m glad he’s back,” says Herbert the pervert. “I don’t know who that month-old jack o’ lantern was, but I didn’t get this brand of humor.”

May 23, 2012

In a Hollywood Reporter interview, Conan says that he and Leno have no relationship: “He certainly isn’t calling me…The odds are we will both leave this Earth without speaking to each other, which is fine. There’s really nothing to say.”

May 17, 2012

Conan appears on Letterman after a 13-year absence. “I think the longer we just sit here, the more uncomfortable it will make Jay,” Letterman snarks after O’Brien takes his seat. “You know Jay’s watching right now,” Conan replies. “He’s getting a live feed in a satellite truck right now, watching every second.” Then, of course, he squeals and shakes his head a la Jay.

August 27, 2012

But Jimmy Kimmel, how do you really feel about Jay Leno? Like this: “F— him,” Jimmy says before a live New York audience.

October 21, 2012

Kimmel to New York Magazine, on the eve of his show moving to an earlier time slot (and going up directly against Tonight and Late Show): “Everyone is better than Leno.”

March 1, 2013

Kimmel gets even more belligerent than usual in a long Rolling Stone interview, declaring that Leno “hasn’t been a good stand-up in 20 years” and noting that “as a comedian, you can’t not have disdain for what he’s done: He totally sold out. He was a master chef who opened a Burger King.” It seems, also, that some of his animosity stems from hurt feelings — in 2008, Leno and Kimmel apparently grew closer when Leno considered moving from NBC to ABC. But when the deal vanished, so did Leno’s calls to Kimmel — leaving the younger host “feel[ing] stupid,” and maybe fueling the vitriol he’s been spewing Leno’s way ever since.

November 22, 2013

On Late Show, Howard Stern tells Letterman that he’s disappointed in Dave for reopening diplomatic relationships with Leno. “I feel like a Vietnam veteran! I feel like I’m still in the jungles fighting your war, and you’ve made up with Vietnam!” Stern exclaims. “Jay Leno will forever blow my mind. This is a guy, he took The Tonight Show from you… Mind you, I work for NBC Television now, and I’m not speaking to Jay Leno. They ask me to go on his show, and I say ‘No, he did Dave wrong.'” And yes, he also adds in a brief, mocking Leno impression.

February 3, 2014

Letterman appears on Howard Stern’s Birthday Bash and says that he and Leno have indeed buried the hatchet — though this doesn’t mean they’re friends. And something tells me we shouldn’t expect Dave to hold back on the night of Jay’s very last show.

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