A 14-year box office record just fell — and, as with so many box office records, this one was claimed by Marvel Studios. Boxoffice Pro presents the top 10 highest-grossing films ever over the extended Labor Day weekend.
Interestingly, four of these films actually debuted on Labor Day weekend, while the other six were already into their sophomore frame or later. In fact, two of these titles were all the way into their fifth frame, yet outgrossed many Labor Day weekend premieres from throughout the decades.
Note: this list is ordered by domestic revenue earned during a film’s extended Labor Day weekend, Friday to Monday. It does not take into account admissions, re-releases, or figures adjusted for inflation.
(Updated in September 2021.)
#1: Shang-Chi and the Legend of the Ten Rings
2021’s Marvel Cinematic Universe (MCU) origin story didn’t just break the Labor Day weekend record, it destroyed it. Taking in $94.6 million, it more than tripled the prior record holder. Starring Simu Liu and directed by Destin Daniel Cretton, the film did so well with its theatrically exclusive release that Disney announced later that same week that all of its remaining 2021 films would receive theatrical exclusivity.
#2: 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 remained unbroken for 14 years.
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.
#3: 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. The film went strong for months, with five weekends at #1 and 15 weekends in the top 10.
#4: Crazy Rich Asians
2018’s romantic comedy based on Kevin Kwan’s novel debuted to a decent but not eye-popping $26.5 million in August 2018. But it would truly make box office history in subsquent weekends, declining only -6.4 percent in its second frame, among the mildest drops in modern box office history, reflecting positive word of mouth and a growing buzz. When the extended Labor Day weekend fell on Crazy‘s third frame, it was still going strong, earning a crazy rich $28.5 million.
#5: Guardians of the Galaxy
2014’s Marvel Cinematic Universe superhero fantasy didn’t reach Labor Day weekend until its fifth frame, by which point it was still earning galactic numbers with $22.9 million. In fact, the film’s weekly gross actually increased +8.6 percent during Labor Day week.
Such stats 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, though its Tuesday release lowered its opening weekend, thus artificially inflating its multiple.)
#6: 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.
#7: 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 fifth-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? The boy band concert documentary One Direction: This Is Us.
#8: 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.
#9: 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 by +8.7 percent during Labor Day week.
#10: 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.
Sequel Don’t Breathe 2 premiered in August 2021, earning $31.3 million as of this writing, as it approaches the end of its run. Labor Day weekend fell on the sequel’s fourth frame, where it earned $2.3 million.