Ricky Oyola, godfather of the east coast “filming a line via just skating random shit on the street”-practice, once expounded on his peak skateboard dream: doing a line through Philadelphia’s then-standing City Hall, into the street, up into the Municipal Services building, back down the stairs, across the street, into Love Park, through Love Park, and end at Wawa.

The closest he got on record was a line from the end of City Hall, through the intersection, and into Love Park in Eastern Exposure 2, but it did establish a lingering precedent for connecting spots. Apart from Ricky and that Joey O’Brien Sabotage 4 line where he starts at Love and ends up in the garage beneath it, spot connecting does not have a rich history in Philadelphia.

Or anywhere, really — because doing a line from one spot, through the street, and to another, is fucking hard. There are variables (people, traffic, pebbles, maybe two sets of security, acts of God), and a pressing anxiety of missing the final trick in an already-long line, which gets amplified by the fact that fifteen other things went right up until that point. As you will soon learn, spot connecting is something most people do for the sake of doing it. In the majority of cases, they stick to their safe tricks.

Like Philadelphia, New York is a dense and layered city. Many of its streets are narrow, and depending on where you are, three or four spots could be across from one another. New York never had a “Big Three,” but it does have three different types of benches on four different street corners, and over the years, skateboarders here have kept their third eyes open and far-sighted.

+++++++

Harold Hunter — N.Y. Revisited (1995 or 1996)

Where: West Broadway & Spring Street

Stats: 13 pushes, 6 tricks…kinda

If he was skating to SahBabii and a JuicePress was visible in the background, Harold’s trick off a curb cut, 180 on flat to switch 180 up a curb, and ender of a diamond-plated 5050 in New York’s eventual Eurotrash capital would look eerily contemporary. The “cruise around Soho” subplot that makes its way into 50-percent of “Summer Trip to New York” montages has more-or-less followed the blueprint envisioned in this line (though Harold’s Whitehall line from Mixtape will forever be his finest choreography work.)

Jamie Thomas — Welcome to Hell (1996)

Where: Brooklyn Banks

Stats: 12 pushes, 6 tricks

Widely accepted as one of the best lines of the era, this one is further elevated by the fact that locals themselves didn’t begin skating handrails until approximately 2016. Yes, the Big Banks and Little Banks are two seperate spots, and the thirteen-stair rail is barely a spot to begin with.

Jason Dilliams — Photosynthesis (2000)

Where: Water Street & Coenties Slip

Stats: 5 pushes, a couple steps, 3 tricks

Subversive line choreography was a blank canvas in 2000. An underutilized fakie front shove, skate across Water Street, kick your board up into your hand, walk down some steps, and at the end of the decade, people are still recounting your deed.

Robert Puleo — Moving in Traffic (2007)

Where: Water Street & Coenties Slip again! Can you believe it?!

Stats: 8 pushes, 3 tricks

Some years and a renovation later, the hallowed ground of Photosynthesis‘ breaking-of-the-code looks strikingly different. A plaza sits atop where the barrier once stood, and the portal into a pissy hell across the street has been sealed.

In his most underrated part, one of the decade’s eminent urban explorers didn’t merely hit the right on Water Street and skate the same cellar door that everyone else was skating in 2007 (see Westgate’s opening line here.)

Nah b. He hit that right. He skated up that lil’ hill, and hauled his I-Paths on over to an under-utilized cellar door across the street, at a deli where the workers would go absolutely crazy on you for skating ;)

Nate Rojas — NY Skateboarding’s “Best Line in New York” Contest (2010)

Where: Brooklyn Banks

Stats: 11 pushes, 5 tricks

Much like 2Pac v.s. Biggie or Lebron v.s. Kobe, skateboarders love debating who actually invented skateboarding: Jamie Thomas or Stephen Berra.

We’re a partisan news outlet; the answer seems clear in the QS office. Is Steven inspiring young skateboarders who are two generations removed to recreate his most iconic achievements (in a modified setting, at that?) Nate battled higher rails, a chain, and what looks like a full 5-on-5 game in the court (as opposed to Jamie skating through it at halftime), to pay tribute to the inventor of the ollie.

Kevin Tierney — Poisonous Products (2011)

Where: Centre and Worth Street

Stats: 14 pushes, 4 tricks (damn right we’re gonna count the switch roll-off)

These two spots are logistically so far from each other that they avoided having the title card for the video at its beginning, and saved it for when Kevin had to push up the hill to get to where Black Hubba starts.

Jerry Mraz — Slappy Hour (2011)

Where: Greenwich Avenue & 12th Street

Stats: 9 assertive pushes, 4 tricks

Even with a hydrant that is over a block away and a homage to one of Mike Carroll’s greatest achievements in spot connecting with the 360 shove/360 flip mid-street combo, the most distance traveled in Mraz’s Slappy Hour part was not this line, but the walk his filmer took 1/4 of the way over the Queensboro Bridge to film a B-roll angle of him back tailing the ledge below (see opening line.)

Leo Gutman — The Brodies (2013)

Where: Worth Street & Baxter Street

Stats: 11 pushes, 3 tricks

This one deserves special mention because it connects what may be the best ledge downtown on the worst ground downtown, across the street, and into the best place to skate flat downtown, which contains the crustiest, most rounded-off ledge downtown.

(And as you have probably caught on by now, skateboarders did not take Jamal Smith’s early 2010s advice re: not doing 360 flips in the middle of every single line.)

Brandon Westgate — Zoo York 20-Year Anniversary Commercial (2013)

Where: Astor Place & Lafayette Street

Stats: 9 pushes, 3 tricks

You gotta give a guy credit for showing up to New York’s greatest non-spot, beginning a line there, skating across the street, and down pretty much an entire block with nothing to skate so he could nollie flip a sewer cap.

Steve Brandi — Static IV (2014)

Where: 52nd Street & 6th Avenue

Stats: 8 pushes, 3 tricks

In their respective heydays, the ultimate New York spot connection would’ve been a line from CBS, across Sixth Avenue, and over to Paine Webber. (Ricky definitely would’ve tried it if he was born in another zip code.) Given the fact that the building extinguished everything there was to skate at CBS bit-by-bit, and Paine Webber is a dusty relic of midtown sessions past, Steve Brandi cutting off ambulance so he could back tail one of New York’s most beautiful slabs of marble is good enough.

Dave Caddo — People’s Temple (2015)

Where: South 2nd Street & Kent Avenue

Stats: 8 pushes, 5 tricks…word to Ben Sanchez, that Chinese ollie counts

As one of skateboarding’s most under-appreciated geniuses, Caddo knew that any spot below a new Williamsburg condo was bound for knobbing not long after its debut. He got this one in before anyone else could, and the first spot’s demise followed shortly thereafter.

Related: The Chillest Lines in Skateboarding History: 1993-1999, 2011-2012