With Tenet to be released domestically in select markets on September 3, the Wednesday before Labor Day, Boxoffice Pro presents the top 10 highest-grossing films ever over the extended Labor Day weekend. Will Tenet soon crack this ranking?
Four of these films debuted on Labor Day weekend, while six were already into their sophomore frame or later.
Note: this list is ordered by domestic revenue earned during a film’s extended Labor Day weekend. It does not take into account admissions, re-releases, or figures adjusted for inflation.
#1: Halloween 
Of the 13 films released or scheduled in the decades-long Halloween horror franchise, most were released in October, as befitting the title holiday. But four came out in August or September, including 2007’s ninth installment, which scared up a $30.5 million Labor Day weekend opening. That record remains unbroken for a dozen years and counting.
More movies are coming: 12th installment Halloween Kills is scheduled for October 15, 2021 and 13th installment Halloween Ends is scheduled for October 14, 2022.
#2: The Sixth Sense
Labor Day arrived in The Sixth Sense‘s fifth frame, as the 1999 supernatural fantasy drama set a then-record for the holiday weekend with $29.2 million. That record would stand for eight years. If adjusting for ticket price inflation, it would remain the Labor Day weekend record holder even today.
#3: Crazy Rich Asians
2018’s romantic comedy based on Kevin Kwan’s novel debuted to a modest $26.5 million in August 2018 before declining only -6.4 percent and -11.5 percent in its second and third weekends, among the mildest drops in modern box office history. When Labor Day weekend fell on Crazy‘s third frame, it was still going strong, earning a crazy rich $28.5 million.
Even as it takes the bronze medal on this list, Crazy earned the top single day Labor Day Monday gross ever, with $6.6 million.
#4: Guardians of the Galaxy
The Marvel Cinematic Universe superhero fantasy didn’t reach Labor Day weekend until its fifth frame, by which point it was still going strong with $22.9 million. In fact, the film’s weekly gross actually increased +8.6 percent during Labor Day week.
Such numbers help explain why Guardians boasts the highest total-to-opening-weekend multiple of any MCU installment released on a Friday at 3.53x, a statistic reflecting word of mouth over time rather than pre-release hype. (Only Spider-Man: Far From Home technically earned a higher multiple, but its Tuesday release lowered its opening weekend and thus artificially inflated its multiple.)
#5: The Possession
Somehow only ranking 18th in the list of highest Labor Day Monday grossers, 2012’s horror flick nonetheless ranks fifth on the Labor Day extended weekend list, opening with $21.0 million.
Why the discrepancy? Because the film only earned 15.8 percent of its extended weekend gross that Monday, far lower than the aforementioned The Sixth Sense with 21.7 percent, Crazy Rich Asians with 23.1 percent, or Guardians of the Galaxy with 25.4 percent.
#6: Lee Daniels’ The Butler
Labor Day weekend 2013 saw a very rare occurrence at the box office: two different films led, depending on whether you counted only the Friday + Saturday + Sunday “regular” weekend or also included Labor Day Monday.
Under the former measure, the biopic starring Forest Whitaker as Cecil Gaines, who served eight presidents during a decades-long tenure as White House butler, was runner-up. Yet thanks to its strong Labor Day Monday—the fourth biggest ever, with $5.3 million—the film took the lead for the extended frame with $20.2 million in its third weekend.
Which film beat it during the regular Fri./Sat./Sun. weekend but fell to second place when including Monday? Read on, because that title also appears later on this list.
#7: Transporter 2
Starring Jason Statham as private driver for hire Frank Martin, the action trilogy’s three installments were released in different months: October, then September, then November. When the middle installment debuted on Labor Day weekend 2005, it earned $20.1 million, the best opening of the three. In fact, it would have boasted the trilogy’s best opening weekend even without that additional Monday.
#8: The Help
Based on the novel by Kathryn Stockett, the historical drama helped itself to $19.8 million on its third weekend. Similar to the aforementioned Guardians of the Galaxy, it actually increased its weekly gross +8.7 percent during Labor Day week.
#9: Don’t Breathe
The horror thriller inhaled $19.7 million on Labor Day weekend 2016, during its second straight frame atop the box office. It ended up as the second-biggest horror title of the year with $89.2 million, behind only The Conjuring 2 with $102.4 million.
#10: One Direction: This Is Us
2013’s concert documentary about the since-disbanded boy band—directed by Super Size Me director Morgan Spurlock, of all people—originally led its Fri./Sat./Sun. weekend with $15.8 million. But its weak Monday, where it only came in fourth, dropped the film to runner-up for the extended weekend, behind Lee Daniels’ The Butler. Still, This Is Us’ $18.4 million total opening qualifies it for this list.