How far will it fly?

That’s been the question on everyone’s mind since the Home Run Derby debuted at the Metrodome in 1985. Of course, we want to see who wins. But there’s also the sheer, jaw-dropping spectacle of a baseball that seems to shake off the constraints of gravity and disappears into orbit.

The Derby is the perfect setting for record-setting home runs. That was never more the case than in the 2021 edition, held at mile-high Coors Field, where the distance-sapping humidor took the night off and records seemed primed to fall.

• Derby history: Looking back at past slugfests

Statcast has been tracking Derby dingers since 2016, and the '21 HRD saw the three longest big flies the system has ever measured, as well as four of the top five and eight of the top 10, with 15 balls reaching the 500-foot mark.

With the 2023 Derby at T-Mobile Park in Seattle hours away, here is an updated look at the longest homers in Derby history, through 2022. First, we’ll rank the five longest since Statcast began tracking, as well as the five longest during that span that didn't have the benefit of taking place at Coors Field. Finally, we’ll round up some memorably gargantuan dingers from Derbies in the pre-Statcast era.

STATCAST ERA (OVERALL)

1) 520 feet -- Juan Soto, 2021 (Colorado)
Soto is a hitting phenom, and on this night, he showed that he can launch a baseball as far as anyone, while making it to the final round. This first-round moonshot into the upper deck in right field is so far the only ball Statcast has tracked at 520 feet or longer. However, Soto's Derby title would have to wait one more year, for the 2022 edition at Dodger Stadium.

2) 518 feet -- Trevor Story, 2021 (Colorado)
Story didn't win the Derby at his home ballpark, but he certainly gave Rockies fans in attendance some thrilling moments. His 20 first-round big flies -- featuring this 518-footer that nearly reached the left-field concourse -- were enough to advance past Joey Gallo.

3) 514 feet -- Pete Alonso, 2021 (Colorado)
The Polar Bear is made for the Derby -- that much is clear. He won in 2019, and when the event returned in '21, he did it again, with relative ease. Alonso mashed four taters of at least 508 feet, including this one that set the tone for his night, early in the first round.

4-T) 513 feet -- Shohei Ohtani, 2021 (Colorado)
There was enormous anticipation for Ohtani's Derby performance, and while Soto defeated him in multiple swing-off rounds, the two-way phenom still put on a spectacular show. The fireworks display included six rockets of 500-plus feet -- two more than all players had hit in the previous four Derbies, combined. This majestic shot to the right field upper deck seemed to almost disappear into space before coming back.

4-T) 513 feet -- Aaron Judge, 2017 (Miami)
Marlins Park was still Giancarlo Stanton’s house in 2017, but Judge unseated his future Yankees teammate as Derby champion, while also launching each of the four longest homers that Statcast had tracked at the event, until 2021. This one soared over all the fans sitting or standing beyond the left-field fence, seemingly testing the boundaries of the stadium itself.

STATCAST ERA (NOT AT COORS FIELD)

1) 513 feet -- Judge, 2017 (Miami)
This one still reigns supreme among those hit at or close to sea level.

2) 507 feet -- Judge, 2017 (Miami)
This blast was a Derby walk-off, giving Judge 13 home runs in the second round to surpass Cody Bellinger’s 12, with a minute still remaining on the clock. It also -- like the one above -- was longer than any homer tracked in an actual game. (That record is held by Nomar Mazara, then of the Rangers, who launched one a projected 505 feet on a windy day in Texas in 2019).

3) 504 feet -- Judge, 2017 (Miami)
This one looked a lot like the previous two and flew nearly as far.

4) 501 feet -- Judge, 2017 (Miami)
Judge was just getting warmed up -- in the first round against Justin Bour -- when he pummeled this one over the home run sculpture that then stood beyond the left-center field wall.

5-T) Giancarlo Stanton: 497 feet, 2016 (San Diego)
It was Stanton’s year in 2016, when he crushed 61 big flies to knock off defending champion Todd Frazier at San Diego’s Petco Park. This second-round bomb appeared to nearly hit the jumbotron looming above the left-field seats.

5-T) Stanton: 497 feet, 2016 (San Diego)
It’s perhaps a bit surprising that Stanton’s personal best for home run distance didn’t come in the Derby, as he hit one 504 feet in a regular season game on Aug. 6, 2016. Then again, that came at Coors Field.

PRE-STATCAST ERA

Comparing the Derby homers below to those that occurred under the watchful eye of Statcast is a bit of an apples-and-oranges situation. Before there was advanced tracking technology, the methodology was different and perhaps less precise and more open to subjectivity. Nor is comprehensive data available in the way it is now.

With that said, the Derby certainly saw some mammoth taters hit before 2016. Here are just some of the most notable examples.

Sammy Sosa: 2000 (Atlanta), ‘02 (Milwaukee)
Slammin’ Sammy knew how to put on a Derby show. He won the event in 2000 in Atlanta, peppering Turner Field’s upper deck and launching an estimated 508-footer to center field, then was the runner-up in 2001 (Seattle) and ‘02, at what was then called Miller Park. Sosa really brought the lumber in the last of those years, supposedly hitting seven balls 500-plus feet, including a 518-footer off the top of the scoreboard, a 520-footer to the upper deck (near Bernie Brewer’s slide) and a 524-footer that actually cleared the slide and left the ballpark.

Frank Thomas: 1994 (Pittsburgh)
The Big Hurt absolutely put a hurting on this ball, which arced off the facing of the top deck in left-center field at Three Rivers Stadium. It was estimated at 519 feet. “I knew I could hit one 500 feet and not come unglued,” Thomas later said. “So when I hit that, I felt like people finally knew.”

Josh Hamilton: 2008 (New York)
The Derby came to the old Yankee Stadium, and Hamilton delivered an awe-inspiring 28 first-round homers, including an estimated 518-footer to the back of the right-center-field bleachers.

Bobby Abreu: 2005 (Detroit)
Abreu isn’t really thought of in the same class as some of these other legendary sluggers, but he stole the show at Comerica Park in 2005, setting (since-broken) records for homers in a round (24) and a Derby (41). Abreu’s longest drive -- to the porch above the back of the right-field seats -- was pegged at 517 feet.

Mark McGwire: 1996 (Philadelphia), ‘98 (Colorado), ‘99 (Boston)
In 1996, Big Mac launched multiple balls into the remote 600 level at Veterans Stadium while battling Barry Bonds. The ‘98 Derby at Coors Field is remembered more for Ken Griffey Jr.’s victory after a last-minute decision to participate, but it was McGwire who had the longest bomb, which flew an estimated 510 feet, over the lower level of bleachers in center field. His Derby moment really came a year later, however, as McGwire captivated Fenway Park, including one drive that Jayson Stark described at ESPN as, “488-foot lunar mission that soared over the Green Monster, cleared the street, carried beyond a parking garage and hit a billboard above the train tracks, right next to the never-reached Massachusetts Turnpike.”

Stanton: 2014 (Minnesota)
Even before Statcast, Stanton was crushing at the Derby. One of his drives landed close to the top of the left field upper deck at Target Field, yielding a projected distance of 510 feet.

Prince Fielder: 2009 (St. Louis)
Prince earned the first of his two career Derby titles in 2009 at Busch Stadium, at one point hitting a ball out of sight, an estimated 503 feet to right-center field. Of course, Prince wasn’t the Derby’s first Fielder. His dad, Cecil, famously hit multiple balls into a bar area in the third deck of center field seats in Toronto in 1991.

Ken Griffey Jr.: 1993 (Baltimore)
It might not be among the absolute longest Derby homers, but it has an argument as the most iconic, so we have to mention it here. Griffey was the epitome of cool in 1993, never more than when he blasted a ball over the right field wall at Camden Yards, across Eutaw Street and off the B&O Warehouse. A plaque still marks the spot, noting an estimated distance of 465 feet. As of 2021, nobody has hit the warehouse on the fly in game action.

Darryl Strawberry: 1986 (Houston)
In just the second Derby held, at the Astrodome, Strawberry hit a ball that was said to have struck a speaker hanging from the roof, about 350 feet from the plate and 140 feet high. The Reds’ Dave Parker, who was there, made the dubious claim that the ball would have gone 550 feet unimpeded.