Static Media
One of the earlier running gags on Matt Stone's and Trey Parker's animated sitcom "South Park" was the repeated, comedic death of Kenny McCormick. Kenny (Stone) was the best friend of Stan (Parker), Kyle (also Stone), and Cartman (also Parker), and he seemed to be the most ... worldly of the four. Kenny's face was usually covered mostly by an outsize orange coat, and all of his dialogue was muffled and incomprehensible. Later, it would be established that Kenny was incredibly impoverished and that he seemed to know a lot more about sex, drugs, and crime than an eight-year-old ought to.
For the first six seasons of the series, from 1997 to 2002, Kenny died in almost every single episode. Kenny's deaths were usually very demonstrative, with the young boy being impaled on a flagpole or cut in half by a chainsaw. When Kenny died, one of his friends would briefly respond, "Oh my God, they killed Kenny!" (with another chiming in with "You bastard!"). Both Kenny's death and the reactive line of dialogue originated in Stone's and Parker's 1992 short "Jesus vs. Frosty," as well as in their much slicker 1995 short film "The Spirit of Christmas." Kenny's death was a cheap, shocking way to get laughs, and it was mostly effective. To add to the grimness of Kenny's many demises, his corpse would often be seen being picked at by rats.
Kenny was also miraculously resurrected at the beginning of every episode, often with no fanfare whatsoever. Sometimes, he merely appeared out of thin air. Then, like clockwork, he would die once again. No one seems to have remembered that he had died many times before.
Eventually, Stone and Parker stopped killing Kenny, and the character now lives to the end of most "South Park" episodes. This, of course, begs the question: how many times did Kenny die? Luckily, we have access to those numbers.
The number of times Kenny died on the South Park TV series
Comedy Central
As mentioned, Kenny died regularly for the first six seasons of "South Park." He was spared in "Mr. Hankey the Christmas Poo" (December 17, 1997) as a show of Christmas mercy, but he was murdered pretty regularly beyond that.
Indeed, sometimes Kenny died multiple times in an episode. In "Pinkeye" (October 29, 1997), Kenny died when a satellite fell on him. When he was being embalmed, a Worcestershire sauce incident brought him back to life as a zombie. Kyle then ended up chainsawing zombie Kenny in half, killing him again. In an epilogue, Kenny once again dug out of his grave, only to have his headstone fall on him. Then a plane crashed into him. Recall that in 1997, a certain brand of "shock" humor was just coming into vogue (largely spearheaded by the success of "South Park") and many comedians began telling jokes that took worn-out 1980s sitcom tropes to violent extremes. Kenny's death was meant to be whimsically shocking in its casual violence.
The continuity of Kenny's deaths is deliberately toyed with regularly. Sometimes, Kenny's death is a big deal, and characters weep for his loss. Other times, it's so commonplace that Stan and Kyle almost sigh their "They killed Kenny" line and walk away as if nothing happened. In the episode "Summer Sucks" (June 24, 1998), there is a flashback to when Kenny was in kindergarten, and he dies in the flashback. He is, however, fine back in the present.
Counting all the multiple deaths over the first six seasons of "South Park," Kenny died or was killed 98 times. This doesn't count the deaths Kenny experienced in the show's title sequence, as those would be difficult to count correctly.
Kenny's deaths in the South Park movie and in shorts
Paramount
In the 1999 feature film "South Park: Bigger, Longer & Uncut," Kenny dies early in the film when he accidentally sets himself on fire after setting his own flatulence alight. At the hospital, the doctor (George Clooney) accidentally replaces his heart with a baked potato, and he dies on the operating table. The film, however, follows Kenny into Hell, where he becomes friends with Satan (Parker) and consoles the Lord of Darkness over his abusive relationship with Saddam Hussein (Stone). Kenny does briefly return to Earth during the film's climax, bids his friends farewell, and ascends to Heaven. That counts as two deaths.
As mentioned, "South Park" began as a pair of Christmas shorts, and a Kenny-like character is killed in "Jesus vs. Frosty." (The character called Kenny in that short resembles the eventual Cartman.) In the 1995 follow-up, Kenny was properly named and he likewise died when Santa Claus accidentally killed him with a psychic blast.
There were also, throughout its history, numerous bumpers, shorts, specials, and original ad spots that Stone and Parker made, and Kenny died in many of them. These were done for "The Tonight Show," the MTV Movie Awards, the movie "The Aristocrats," and other such special events. In all the shorts and specials, about 22 in all, Kenny died an additional 14 times. Jay Leno's chin even killed him once.
If one wanted to be especially liberal, one could also include the few "South Park" video games, all done with Stone's and Parker's participation. Kenny, in the course of the video games' stories, was offed another 14 times. 98 (TV series) + 14 (specials and shorts) + 14 (video games) + 2 (the movie) = 128. Kenny has died a total of 128 times. Again, this is not counting the title sequence from seasons 7 through 11 where he was killed by Death. If you want, tack on those additional 71 instances, making a grand total of 199.
Why South Park creators Matt Stone and Trey Parker stopped killing Kenny
Comedy Central
After a while, Matt Stone and Trey Parker began to tire of killing Kenny, and even took his death very seriously in the episode "Kenny Dies" (December 5, 2001). Kenny was hospitalized after being diagnosed with muscular dystrophy, and his friends had to face the sadness of actually losing a friend. Tragically, Stan was out of the room when Kenny actually passed, and Kenny's last words were "Where's Stan?" Stan became deeply depressed after that.
On a DVD commentary track, Parker and Stone explained that Kenny had become too much of a comic "prop," and his death was becoming tiresome for them to write over and over. They also had become fans of newer characters like Butters (Stone) and Tweek (Stone) and wanted to give them more screen time. After "Kenny Dies," Kenny was out of the show for the bulk of the show's sixth season. He essentially stayed dead, save a few appearances as a ghost. In the sixth season finale, "Red Sleigh Down" (December 11, 2002), Kenny was brought back officially (again, with no fanfare whatsoever), and he has stayed alive (mostly) ever since.
Cheekily, Stone and Parker decided, many years later, to canonically explain why Kenny died so many times. In "Cartman Joins NAMBLA" (June 21, 2000), Kenny dies, but his parents give birth to a little brother ... that they also name Kenny. Contrary to this explanation, however, are the events of the episode "Mysterion Rises" (November 3, 2010). In that episode, it's explained that Kenny's parents belonged to a cult that worshiped the powerful Lovecraftian Elder God Cthulhu. Kenny, through their participation, became cursed, nay fated to die every day, only to wake up, fully clothed, the following morning. The immortality curse also entailed that anyone who witnessed his death would forget about it. Kenny is stabbed to death in that episode as well. No one remembers it.