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The Daytona 500 is, bar none, the crown jewel of the NASCAR Cup Series season.

In fact, no race even remotely compares to the 500 — appropriately nicknamed “The Great American Race” — in terms of grandeur, notoriety, and prestige.

But even with all the buzz and excitement surrounding the annual kickoff event to the Cup Series campaign, it’s not guaranteed that every Daytona 500 is going to go perfectly according to plan. After all, this year marks the 65th running of the marquee event, so in its past 64 installments, something was bound to take a wrong turn at some point.

Up next, we’ll look back on two Daytona 500s that went completely off the rails for unforeseeable reasons, and then we’ll reflect on one 500 that ended up being such a total dud that it angered arguably the sport’s best driver ever.

The infamous pothole incident at the 2010 Daytona 500

Jamie McMurray won the 2010 Daytona 500, holding off Dale Earnhardt Jr. in a close finish to a competitive race that featured 52 lead changes and four multi-car wrecks.

But to this day, this race is remembered more for a pesky pothole that resulted in two red-flag stoppages totaling two hours and 24 minutes for track repairs that left many TV viewers and in-person spectators feeling irritated and restless.

The hole, which appeared between turns 1 and 2 on the high-banked 2.5-mile superspeedway, likely had a lot to do with the fact that Daytona’s aging asphalt racing surface had last been repaved in 1978. The combination of cooler-than-usual temperatures and rain that had soaked the track earlier in the weekend probably didn’t help either.

Thankfully, track officials’ second attempt to fill in and smooth over the pothole worked at least enough for drivers to run the final 32 laps without any more pothole-related setbacks. But it was the pothole — not race-winner McMurray or runner-up Earnhardt or anyone else — that stole the show and left a stain on an otherwise enjoyable afternoon.

Juan Pablo Montoya’s notorious collision with a jet dryer at the 2012 Daytona 500

As if it wasn’t bad enough that the 2012 Daytona 500 had become the first 500 in the race’s 54-year history to be postponed from Sunday to Monday because of rain, matters took a substantially direr turn once the race actually began on Monday night.

In one of the most bizarre moments not only in Daytona 500 history but in the history of NASCAR, driver Juan Pablo Montoya had a part break on his No. 42 Chip Ganassi Racing Chevrolet and abruptly crashed into a jet dryer while under caution, igniting a massive fire.

As the jet dryer burst into flames and spilled about 200 gallons of jet fuel onto the track, the inferno quickly spread to the racing surface and required immediate action on the part of safety crews, who rushed to extinguish the blaze but needed more than two hours to repair the track good enough for the race to resume.

Thankfully, neither Montoya nor the driver of the jet dryer was hurt in the accident. Matt Kenseth went on to win his second Daytona 500 in four years, but the outcome was a mere footnote to the Montoya-jet dryer collision, which ultimately led to one of the most famous tweets in NASCAR history — which you can see above.

The painfully humdrum 2000 Daytona 500 even ticked off Dale Earnhardt

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The 2000 Daytona 500 was significant for a few reasons. For one, it marked Dale Earnhardt Jr.’s first appearance in The Great American Race and the official kickoff to the third-generation driver’s much-anticipated rookie season in NASCAR’s premier series.

But it was another Dale — reigning Cup Series champion Dale Jarrett — who took the win, scoring his third Daytona 500 triumph since 1993.

But due to a brand new superspeedway rules package that required that all teams use the same shock absorbers in an effort to slow the cars and make the racing safer, this was arguably the most anticlimactic Daytona 500 of all time. Not only did drivers find it nearly impossible to pass as the race featured just nine lead changes — far below the Daytona 500 norm — but one driver, Jarrett, led nearly half the laps in his No. 88 Robert Yates Racing Ford. 

Among the most vocal critics of the much-maligned rules package was seven-time Cup Series champion and 1998 Daytona 500 winner Dale Earnhardt, who finished 21st.

“That’s the worst racing I’ve seen at Daytona in a long, long time,” Earnhardt said, as recorded in a throwback YouTube video. “They took NASCAR Winston Cup racing and made it some of the sorriest racing. They [NASCAR] took racing out of the driver’s and the crew’s hands. We can’t adjust, we can’t make our cars drive like we want. They just killed the race at Daytona. That’s all I’ve got to say.”

But Earnhardt actually wasn’t quite done voicing his opinion.

“Mr. Bill France Sr. [NASCAR’s late founder] would probably roll over in his grave if he’d seen that deal,” Earnhardt said as he stormed away from a throng of reporters.