In the beginning we see Derice Bannock (Leon) running across the island of Jamaica. Derice is training for the 1988 Olympic Games, and Derice hopes to be a gold-medal winner just like his father.
Before the trial run, Derice visits his friend Sanka Coffee (Doug E. Doug), who is competing in a pushcart race. Sanka wins the race but ends up crashing just after he crosses the finish line, to everyone's amusement.
Later that day, Sanka joins Derice's family at the track for the Olympic run. Derice is preparing to race, meeting a few other competitors-including one short man named Junior Bevil (Rawle D. Lewis). The race starts off great, but halfway across the track Junior stumbles and trips several runners, including Derice. Derice stumbles back to his feet as the finish-line tape is broken, watching his dreams go up in smoke...
Derice confronts Coolidge (Winston Stona), the man in charge of the Jamaican Athletic competition. He begs for a chance to run again but he refuses. Derice then notices a photo of his father on his wall, next to an unfamiliar man. Coolidge identifies the man as Irving Blitzer, an American now living on the island. He had tried to convince his father, Ben to compete in bobsledding. Derice, seeing another chance to compete as a bobsledder, takes the picture and goes to meet with Irv.
Sanka hears about Derice's idea. At first he is excited but balks upon learning that bobsledding is a WINTER sport. Eventually Sanka is persuaded to help his best friend. The two men find Irv Blitzer (John Candy) working as a bookie in a run-down pool hall. He is far from eager to help them, and does not want anything to do with the sport of bobsledding. However, the two men doesn't give up. Upon learning that Derice is the son of his old friend & colleague, Irv relents.
Next day, Irv tries to recruit additional team members. The first newcomer is a bald man Sanka recognizes from the Olympic running trials. The man (Malik Yoba) introduces himself as Yul Brenner, and is more than willing to compete in bobsledding so long as it leads him to the Olympics. Only one other man shows up to join the sled team- Junior, the clumsy runner from the track. Yul is immediately hostile to Junior (he was one of the other runners tripped up by Junior's fall) but relents since without Junior they don't have a full team.
Irv begins training the four immediately. He builds a makeshift bobsled and has them push it down a steep slope, telling the team that if they can't get a push-start completed in under 6 seconds, they won't have a chance at competing. Yul is the second mildde man, Junior is the first middle man. Irv chooses Sanka as brakes, but he argues with it. He reminds him that the driver in bobsledding has alot more responsiblities than a push car racer and can't go out to have fun with his teammates. Sanka relents and decides Derice could be the driver.
After the first day of training, Junior returns home with the intention of telling his father about the team. But Mr. Bevil (Charles Hyatt) comes home and tells Junior that he has gotten his son a job with a brokerage house in Miami, which he is expected to take by the end of the month. Junior clams up and cannot say anything more.
Initially, the Bobsled training does not go well. The group stumbles and falls several times, not even able to get into the sled. But, after several tries they climb in together and rocket down the mountain, eventually crashing into a police car. Irv runs after the team cheering- they got started in 5.9 seconds! He tells them to bring the sled up on the mountain, making the team groan.
Now that the team is in good shape, Irv goes to Coolidge to ask for funding to get to the Olympics. But Coolidge refuses, thinking that the team will be humiliated. Derice is not shaken, he decides they will try to get the money elsewhere. After several fund-raising endeavors, they are far short of the goal. Junior comes back to the team after a day away, announcing that he has sold his car to get the required funds. Derice does not want to take the money from Junior at first, thinking it to be too much. But Junior explains that he still feels guilty for costing Derice and the others their first Olympic chance, and gladly gives up the money.
The team heads out to Calgary for the Olympic Games. Irv adjusts to the environment easily, but the Jamaicans are unprepared for the severely-cold weather. They buy heavy-duty coats as soon as the plane lands.
Irv registers the team for competition, and meets a few colleagues from his days in bobsledding. Irv has lunch with one friend, Roger (Paul Coeur) and asks for a sled so his team can compete. Roger is reluctant but agrees to sell off an old backup sled from the US team.
The team begins learning how to move & walk on ice, using a hockey rink for practice. It does not go well at first, but they eventually make progress. That night, Derice watches the Swiss bobsled team practicing. He becomes enamored with their efficient performance.
Irv shows off the sled he purchased to the team - it is rusted and old but still works fine.
On their first day at the track, the Jamaican team is met with ridicule and scorn by other competitors. Irv tells them that a push-start will not be necessary for the initial run; they will just be nudged down the slide instead. The run starts off fine but the sled ends up crashing before the finish line. Their next run does not go well either; the Jamaicans end up chasing the sled down the track. A photographer snaps a picture of the group running after the sled, and it makes the papers. This doesn't sit in well with Mr.Bevil and Cooledge.
Derice is repairing the sled when he meets one of Irv's old colleagues. Derice finds out that during the1972 competition, Irv hid weights at the bottom of the bobsled to accelerate its speed. As a result, he was kicked out and had his gold medals revoked.
The following night at the hotel, Sanka tries to pose as a maid, but Yul brushes him aside, thinking he's insane. Junior receives a telegram from his father - the news story about the Jamaican team had alerted Mr. Bevil to his activities and he is now ordering his son home.
While they are out in a bar that night, Yul encourages Junior to stand up for himself. He immediately responds by confronting the German team members who had insulted their team. This results in a huge bar-fight between Yul, Sanka, Junior and the Germans.
At the Relax Inn Motel, Derice berates his teammates for what happened and tells them the Swiss team would never resort to stunts like that because they're awlays focused on their performance. Yul, Sanka and Junior don't take him seriously and continued snickering. Sanka makes a crude joke about the Swiss team and what happens if they try to push a pretty girl off the ice. A few minutes later, Irv comes in and berates the three for not taking things seriously. He reminds them that everyone hates them and they need to get their act together.
After thinking things over, the Jamaicans resume serious training once more. With Irv's help, they are quickly whipped back into shape.
Finally, the night of the Jamaican team's qualifying run has arrived. Irv presents the team with special competition suits as a reward for their changed behavior. Irv then meets with the 3 judges, who remind him that the team must make it off the slope and across the finish line in under 1 minute in order to be eligible. The team sets out, and despite a few bumps they get across the line safely. After several tense moments, their time is revealed: 59.46! Irv & the team are overjoyed at their success.
The guys celebrate by painting their sled with Jamaica's colors. Derice decides to christen the sled "Cool Runnings." At that moment, Irv gets a letter from the judges - the Jamaican team has been disqualified.
Irv angirlly storms into the offices of the men in charge, demanding to know why. Apparently, there is a rule stating that a team must compete in an international race to qualify. Previously, an Olympic trial would be considered an international race, but this time the committee decided to change the rules. However, he isn't fooled and immediately knows the truth - his former coach(from the '72 Olympic Winter Games and currently a primary judge of the '88 Olympic Winter Games) Kurt Hemphill is still punishing him for embarrassing the U.S.A by cheating. Irv confronts his coach and confesses that 16 years ago, he made the biggest mistake of his life. He resorted to cheating because he wanted to win and didn't care what the consequences were. Instead, he ended up disgracing the Americans by embarrassing everyone(including his coach, teammates his friends and family) and his gold medals were revoked as a result. Irv also reminds Kurt that it was HIS mistake and if he wants revenge, he should do it to him because he screwed up, not the Jamacian bobsledding team. They deserve to represent their country by competing in the Winter Games as contenders and doesn't deserve to suffer because of his past mistakes. That night at their hotel, the team gets a phone call. The committee has reverse their decision - the Jamaicans are back in!
Everyone on the island of Jamaica watches the bobsled team wave their flag as they enter the Olympic stadium. After the opening ceremony, Irv tries to find some inspirational words for the team. But this conversation is cut short by the arrival of Mr. Bevil, who has come to collect his son.
He tells Junior that he is only looking out for his sons' best interest, and demands the young boy to gather his things. He draws on Yul's advice and stands up to his father. He tells his father he's staying with his team because he cared about his own interest in making himself look good more than his son's. Junior tells him he's an Olymic athlete now, not his puppet and sends Mr.Bevil on his way.
On the first day of competition, the Jamaican team is scheduled last. Derice tries to psyche up his team, imitating the behavior of the Swiss again. The team begins their run, essentially stumbling down the track and bouncing off the edges. Their end run time is 58.04, landing the Jamaicans in last place.
Derice again tries to imitate the Swiss, but the team is fed up with his attitude. Sanka immediately sets him straight by pointing out that they cannot copy the movements of another team; they must get their own style. Derice insists that he just wants to be the best they can be. Sanka counters that "the best [they] can be is Jamaican," and that they didn't come all this way to forget about their heritage. Derice relents after realizing that his friend and their teammates were right.
On the second day of competition, the Jamaican team is psyched up for sledding. They pull together a push-start within a fraction of their previous time, and wind up getting off even faster than the Swiss team. Their finishing time is 56.53, rocketing the Jamaicans into 8th Place! They are now considered high contenders for the medal.
That night while studying the track, Derice asks Irv about why he cheated. He explains that he'd become so focused on winning that he couldn't picture life without it, a horrible thing for an athlete to do. Irv tells Derice that he doesn't want him making the same mistakes that he made 16 years earlier. He tells him to focus on what happens tomorrow.
The last day of competition arrives, and the fans are eager to see Jamaica's performance. They start off with an even better formation than yesterday, but the ancient sled is unknowingly in poor shape. A bad bounce sends the sled careening out of control, and eventually the sled turns over-sending the team on a terrible out of control path.
When the sled finally skids to a stop, several tense seconds pass before the team even moves. Finally, Derice regains consciousness and sees the finish line mere feet away. Paramedics rush down to tend to the Jamaicans - only to part as they rise to their feet. The guys hoist the sled over their shoulders and begin walking toward the finish line, determined to finish the race no matter what.
The crowd, awestruck by the Jamaicans performance, claps and cheers them on as they finish. Everybody, even Mr. Bevil (now wearing a Jamaican souvenir shirt) - shows their appreciation. Even though their chances of winning are gone, Jamaica finishes with dignity and pride.
Text at the end reveals that Derice, Sanka, Junior and Yul returned to Jamaica as heroes - then four years later returned to the Olympics as equals.