52 Must-Watch Skateboard Videos: A Chronological Journey Through Skateboarding History

Skateboard videos are more than just entertainment; they’re a source of inspiration, a motivator to grab your board, and a way to connect with the culture. Whether you’re seeking motivation, reminiscing about the past, or just want to see some incredible skating, this list of the best skateboard videos ever made, presented in chronological order, will get you stoked. We’ll explore the evolution of skateboarding through the lens of these iconic films, starting from the early days and moving through the different eras that shaped modern skateboarding.

A collage of various skateboard video coversA collage of various skateboard video covers

Table of Contents

The Golden Age of Skateboarding: Classic Videos

Let’s delve into the classics that laid the groundwork for modern skateboarding. These videos, from the 80s and 90s, not only showcased incredible talent but also pushed the boundaries of what was thought possible on a skateboard, inspiring countless generations of skaters.

1. The Bones Brigade Video Show (1984)

The granddaddy of all skate videos, The Bones Brigade Video Show, directed by Stacy Peralta and Craig Stecyk, is a must-see for any skateboard enthusiast. While the picture quality is certainly dated (it was VHS after all!), the sheer talent on display is timeless. This video introduced the world to vert and pool skating and showcased early flatland tricks by Rodney Mullen, setting a foundation for what was to come.

Featured Skaters: Steve Caballero, Tony Hawk, Mike McGill, Lance Mountain, Rodney Mullen, Stacy Peralta, Per Welinder.

2. Powell Peralta – The Search for Animal Chin (1987)

Another iconic video from the Bones Brigade, The Search for Animal Chin, presented a different approach with a storyline. Although some find it a bit corny now, it was groundbreaking at the time and showcased vert skating on a huge scale. The recent 30th-anniversary reunion of the original crew on a rebuilt version of the legendary ramp is a testament to this movie’s lasting impact. The movie is not only about skating, it’s about friendship.

Featured Skaters: Lance Mountain, Mike McGill, Steve Caballero, Tommy Guerrero, Tony Hawk.

3. H-Street – Shackle Me Not (1988)

This video demonstrates how hardcore vert, pool, and street skating were combined into one video. Shackle Me Not features mind-blowing skating, especially when considering the limitations of the era. The impact of Matt Hensley, Danny Way, and Tony Magnusson cannot be understated, and H-Street remains a highly respected name in skateboarding.

Featured Skaters: Aaron Vincent, Art Godoy, Ben Job, Brennand Schoeffel, Brian Lotti, Carl Hyndman, Chris Livingston, Danny Way, Darrin Kimura, Dave Andrecht, Dave Sornson, David Nielsen, Eddie Elguera, Jason Richardson, Jeff Klindt, and many more.

4. H-Street – Hokus Pokus (1989)

H-Street took things a step further with Hokus Pokus, which pushed skateboarding to new heights, especially with Dave Graves’ revolutionary 360 flip down 7 stairs. This video marked a turning point and ushered in a new era of technical street skating. It’s a shame that Matt Hensley quit pro skating after this video, but his impact remains timeless.

Featured Skaters: Ben Job, Brian Lotti, Chris Livingston, Colby Carter, Danny Way, Dave Donalson, Dave Sornson, David Nielsen, Eddie Elguera, John Deago, John Sonner, Kien Lieu, Matt Hensley, Mike Carroll, Ron Allen, Ryan Monihan, Sal Barbier, Steve Ortega, Tony Magnusson.

5. Blind – Video Days (1991)

Directed by Spike Jonze, who later became a renowned film director, Video Days is one of the most influential skate videos ever made. It set new standards in skate film production and is considered a documentary on the shift in skateboarding from corporate vert competitions to street skating. Mark Gonzalez’s skating is still amazing to watch.

Featured Skaters: Mark Gonzales, Rudy Johnson, Jason Lee, Guy Mariano, Jordan Richter.

6. Alien Workshop – Memory Screen (1991)

Alien Workshop’s first skate video, Memory Screen, was ahead of its time, with its experimental Super 8 format, creative editing, and a killer soundtrack. The video showcases innovative skating in vert, street, and technical styles, cementing its place as a classic.

Featured Skaters: Rob Dyrdek, Steve Claar, Scott Conklin, John Pryor, Thomas Morgan, Bo Turner, Duane Pitre.

7. Plan B – Questionable (1992)

Plan B’s Questionable is an iconic video that showcases some of the best skaters of the time. With master Rodney Mullen, Pat Duffy’s smooth style, and Colin McKay skating vert, it is considered a holy grail among skateboarders, showcasing what was to come.

Featured Skaters: Sal Barbier, Mike Carroll, Pat Duffy, Ryan Fabry, Matt Hensley, Rick Howard, Colin Mckay, Rodney Mullen, Sean Sheffey, Danny Way.

8. 101 – Snuff (1993)

Snuff, with a young Jason Dill, was a short, intense video with groundbreaking tricks performed with incredible style and accuracy. Gino Iannucci and Dill changed the game with their speed and execution. This video, promoted with a controversial cover, remains influential to this day.

Featured Skaters: Adam McNatt, Andy Stone, Gabriel Rodriguez, Gino Iannucci, Jason Dill.

9. Girl Skateboards – Mouse (1996)

Featuring a young Eric Koston, along with Rick Howard and Mike Carroll, Mouse is one of the best skateboard videos ever made, with skits and street skating. Directed by Spike Jonze, the movie is based on a German novel and the raw and natural skating is a must-see. Guy Mariano’s part always gets the viewers stoked.

Featured Skaters: Ben Sanchez, Chico Brenes, Daniel Castillo, Eric Koston, Gabriel Rodriguez, Gino Iannucci, Guy Mariano, Jeron Wilson, Jovontae Turner, Keenan Milton, Mike Carroll, Mike York, Richard Mulder, Rick Howard, Rudy Johnson, Sean Sheffey, Shamil Randle, Tim Gavin, Tony Ferguson.

A collage of various skateboard video coversA collage of various skateboard video covers

10. Toy Machine – Welcome to Hell (1996)

Another gem from 1996, Welcome to Hell from Toy Machine, is a raw and gnarly compilation of street skating, especially Mike Maldonado’s footage. Ed Templeton shows the audience some fast and smooth grinds while Elissa Steamer shows that she is capable of destroying any obstacle.

Featured Skaters: Mike Maldonado, Elissa Steamer, Brian Anderson, Satva Leung, Donny Barley, Ed Templeton, Jamie Thomas.

11. Underachievers – Eastern Exposure 3 (1996)

Shot primarily on the east coast in cities like Philadelphia and New York, Eastern Exposure 3 is an action-packed video full of raw street skating. Dan Wolfe filmed, edited and produced this video, originally in black and white, but there’s also a color version.

Featured Skaters: Donny Barley, Jerry Fisher, Reese Forbes, Tim O’Connor, Ricky Oyola, Jahmal Williams.

12. World Industries Trilogy (1996)

The World Industries Trilogy combined three teams: 101, Blind, and World Industries. This video was an attempt to create something spectacular by bringing together the best skateboarders. And they succeeded, making it a classic in skateboarding history.

Featured Skaters: Clyde Singleton, Daewon Song, Enrique Lorenzo, Gideon Choi, Gino Iannucci, Jason Dill, Josh Kasper, Kareem Campbell, Lavar McBride, Marcus McBride, Maurice Key, Ronnie Creager, Sam Devlin, Shiloh Greathouse.

13. Shorty’s – Fulfill the Dream (1998)

Fulfill the Dream showcases some rad technical skating, including Chad Muska, who had recently joined the team from Toy Machine. With new types of tricks such as ending slides with a flip, this video is an example of raw and gnarly skateboarding.

Featured Skaters: Aaron Snyder, Brandon Turner, Chad Muska, Jesse Silvey, Peter Smolik, Sammy Baptista, Steve Olson, Toan Nguyen.

14. Zero – Misled Youth (1999)

Zero’s Misled Youth, a raw video showing insane tricks, became an iconic video in skateboarding. Jamie Thomas’s part is just insane and has made the video one of the best they ever made.

Featured Skaters: Adrian Lopez, Erik Ellington, Jamie Thomas, Jim Greco, Jud Ferguson, Matt Mumford, Ryan Bobier.

15. Emerica – This is Skateboarding (2003)

This is Skateboarding is a mixture of frustration and accomplishment. The video showcases the skills of a young Bryan Herman and the team who pushes the boundaries of skateboarding. This video is hardcore street skating at its finest.

Featured Skaters: Aaron Suski, Andrew Reynolds, Austin Stephens, Braydon Szafranski, Bryan Herman, Chris Senn, Darren Navarrette, Ed Templeton, Erik Ellington, Heath Kirchart, Kevin Long, Leo Romero, Matt Allen, Tosh Townend.

16. Birdhouse The End (1998)

Directed by Jamie Mosberg, The End, was released in 1998 and re-released in 2001. This live-action documentary film had a big budget and shows short stories with Bucky Lasek killing Tony Hawk for the number 1 spot. With the amazing skating of Rick McCrank, Andrew Reynolds, and Steve Berra, this is a must-see.

Featured Skaters: Ali Cairns, Andrew Reynolds, Brian Sumner, Bucky Lasek, Heath Kirchart, Jeff Lenoce, Jeremy Klein, Rick McCrank, Steve Berra, Tony Hawk, Willy Santos.

The Evolution Continues: Skateboarding in the 2000s

The 2000s brought new styles and techniques, pushing skateboarding further. Here are some of the must-watch videos from that era.

17. Transworld – Modus Operandi (2000)

Modus Operandi is another video that felt ahead of its time, with an amazing line by Mike Carroll. The audio-visual compositions, voice-overs, music, and night skating make this video special.

Featured Skaters: Brian Anderson, Chany Jeanguenin, Marc Johnson, Mike Carroll.

18. eS – Menikmati (2000)

This video takes the viewers on a journey to visit spots from all over the world, with documentary-style footage. Tom Penny’s skating stands out, as well as Eric Koston’s part. Menikmati has a relaxing soundtrack with unbelievable vert skating.

Featured Skaters: Arto Saari, Bob Burnquist, Eric Koston, Rick McCrank, Rodrigo TX, Ronnie Creager, Tom Penny.

19. Baker – Baker 2G (2000)

Baker wasn’t a company when this video came out, but it made a huge impact. Baker 2G is all about raw street skating, bloody decks, and a couple of skits.

Featured Skaters: Ali Boulala, Andrew Reynolds, Brad Hayes, Brian Sumner, Dustin Dollin, Elissa Steamer, Evan Hernandez, Heath Kirchart, Jeff Lenoce, Jim Greco, Knox Godoy, Mike Maldonado, Terry Kennedy.

20. Alien Workshop – Photosynthesis (2000)

This video introduced the world to talents like Mark Appleyard and was the beginning of the careers of Anthony Pappalardo and Brian Wenning. Photosynthesis also shows parts from Jason Dill, Josh Kalis, Danny Way, and Tim O’Connor.

Featured Skaters: Anthony Pappalardo, Anthony Van Engelen, Brian Wenning, Danny Garcia, Danny Way, Fred Gall, Jason Dill, Josh Kalis, Kerry Getz, Mark Appleyard, Pat Corcoran, Rob Dyrdek, Rob Pluhowski, Tim O’Connor.

21. Deca – 2nd to None (2001)

A bit different and very creative, 2nd to None, features skateboarding in a warehouse where stuff is build for the video. Daewon Song’s part is a must-watch and the video also features raw technical street skating.

Featured Skaters: Brian Hoard, Chris Haslam, Cooper Wilt, Daewon Song, JB Gillet, Luis Cruz, Marcus McBride, Shiloh Greathouse, Shin Okada.

22. Globe – Opinion (2001)

Rodney Mullen shows his pure and natural skateboarding, followed by amazing vert skating by Renton Miller and Ben Pappa. Chet Thomas also adds technical street skating to this video, resulting in an amazing compilation.

Featured Skaters: Ben Pappas, Chad Fernandez, Chet Thomas, Danny Gonzalez, Gershon Mosley, Jayme Fortune, Matt Mumford, Mike Peterson, Renton Millar, Rodney Mullen, Ryan Kenreich.

23. Transworld – In Bloom (2002)

In Bloom is a video that feels well thought out, with voice-overs, great camera work, and music. The video starts with the skating of Evan Hernandez, followed by Tony Trujillo and Chris Cole, which makes this video a great classic.

Featured Skaters: Alex Gall, Chris Cole, Evan Hernandez, Mikey Taylor, Paul Rodriguez, Tony Trujillo.

24. Coliseum – PJ Ladd’s Wonderful Horrible Life (2002)

Wonderful Horrible Life, made by Coliseum Skate shop, shows the unique talent of PJ Ladd, with great style and performance. Other skaters making an appearance are Ryan Gallant, Jereme Rogers, and Alexis Sablone, who also started their careers by being featured in this video.

Featured Skaters: Alexis Sablone, Colin Fiske, Jereme Rogers, PJ Ladd, Ryan Gallant, Southie.

25. Flip – Sorry (2002)

Sorry from Flip was well received and became an iconic video for kids growing up in the 2000s. With the famous clips of Ali Boulala and Geoff Rowley, this video stands the test of time.

Featured Skaters: Alex Chalmers, Ali Boulala, Arto Saari, Bastien Salabanzi, Geoff Rowley, Mark Appleyard, Rune Glifberg, Tom Penny.

26. Transworld – Chomp on This (2002)

Chomp started as a couple of friends filming each other and ended up as a masterpiece thanks to talented cinematographers, photographers, and artists.

Featured Skaters: Ako Jefferson, Atiba Jefferson, Gabe Morford, Eric Koston, Jamie Thomas, Giovanni Reda, Henry Sanchez, Lee Dupont, Marcus McBride, Lee Dupont, Ty Evans.

27. Zero – Dying to Live (2002)

Dying to Live by Zero shows the great skating of Chris Cole and Jamie Thomas, also included is a slam section that shows some painful moments of the skaters.

Featured Skaters: Adrian Lopez, Chris Cole, Jamie Thomas, John Rattray, Jon Allie, Lindsey Robertson, Matt Mumford, Ryan Bobier, Ryan Smith.

28. Girl – Yeah Right (2003)

Another video directed by Spike Jonze, Yeah Right, made history by using ultra-slow motion and special effects using green screen technology. The video features a cameo by Owen Wilson and is a great and long compilation of skateboarding.

Featured Skaters: Brandon Biebel, Brian Anderson, Chico Brenes, Chris Roberts, Daniel Castillo, Eric Koston, Gino Iannucci, Jereme Rogers, Jeron Wilson, Jesus Fernandez, Justin Eldridge, Keenan Milton, and many more.

A collage of various skateboard video coversA collage of various skateboard video covers

29. Flip – Really Sorry (2003)

Really Sorry is Flip’s second skate video, with epic skating by the team. This video was released prior to Extremely Sorry.

Featured Skaters: Ali Boulala, Arto Saari, Bastien Salabanzi, Danny Cerezini, Geoff Rowley, Mark Appleyard, PJ Ladd, Tom Penny.

30. Darkstar – Battalion (2003)

Sven Kilchenmann and Guy Kampfen demonstrate their technical street skating while Chet Thomas shows some amazing skills in Battalion.

Featured Skaters: Chet Thomas, Chris Dobstaff, Gailea Momolu, Guy Kampfen, Mike Hastie, Paul Machnau, Ryan Kenreich, Sven Kilchenmann, Windsor James.

31. Habitat Mosaic (2003)

Habitat Mosaic is a raw street skating video with a team of talented skaters, with a good balance between filming, music, and editing. The stars of this video are O’Connor, Getz, Janoski, and Pappallardo.

Featured Skaters: Anthony Pappalardo, Anthony Van Engelen, Brian Wenning, Danny Garcia, Danny Renaud, Danny Way, Ed Selego, Fred Gall, Heath Kirchart, Jason Dill, Kerry Getz, Rob Pluhowski, Stefan Janoski, Steve Berra, Ted DeGros, Tim O’Connor.

32. Almost – Round 3 (2004)

After Round 1 and 2, Almost released Round 3, which featured legendary skaters Daewon Song and Rodney Mullen, along with other skaters. This video is known for its consistency and inspirational skating.

Featured Skaters: Chris Haslam, Cooper Wilt, Daewon Song, Greg Lutzka, Rodney Mullen, Ryan Sheckler.

33. Foundation – That’s Life (2004)

That’s Life is a raw grinding video, which is opened by Leo Romero. This is a nostalgic street skating experience.

Featured Skaters: Angel Ramirez, Corey Duffel, Daniel Shimizu, Ethan Fowler, Gareth Stehr, Justin Strubing, Leo Romero, Matt Allen, Mike Rusczyk, Tony Silva.

34. Blind – What if (2005)

What If was released 13 years after Video Days, and it is a raw and gnarly skate video with old-school footage of Ronnie Creager as a kid.

Featured Skaters: Ronnie Creager, Markovich, Craig, Sheppard, Brown, Duncombe, Aaron Artis, Evan Schiefelbine, Patterson, Carlos Ru.

35. Almost – Cheese and Crackers (2006)

Cheese and Crackers features mini-ramp skating by Chris Haslam and Daewon Song. This is a must-watch for mini-ramp fans.

Featured Skaters: Chris Haslam, Daewon Song.

36. Enjoi – Bag of Suck (2006)

Bag of Suck showcases the creative era of skateboarding with Enjoi skateboard team, with skaters who focus on enjoying their session.

Featured Skaters: Caswell Berry, Clark Hassler, Jason Adams, Jerry Hsu, Jose Rojo, Louie Barletta.

37. Lakai – Fully Flared (2007)

Fully Flared from Lakai was one of the first videos shot in HD and took over four years to make. The video won the best skateboard video of 2007. With the skating of Guy Mariano and Eric Koston, this video set new standards for skateboarding.

Featured Skaters: Alex Olson, Anthony Pappalardo, Brandon Biebel, Cairo Foster, Danny Brady, Eric Koston, Guy Mariano, JB Gillet, Jeff Lenoce, Jesus Fernandez, JJ Rousseau, Lucas Puig, Marc Johnson, Mike Carroll, Mike Mo Capaldi, Nick Jensen, Rick Howard, Rob Welsh, Scott Johnston.

38. Emerica – Stay Gold (2010)

Stay Gold was released seven years after This is Skateboarding, and this video is a worthy successor. It is a cinematic experience with many legendary skaters.

Featured Skaters: Aaron Suski, Andrew Reynolds, Ben Krahn, Brandon Westgate, Braydon Szafranski, Bryan Herman, Chris Senn, Collin Provost, Ed Templeton, Heath Kirchart, Jamie Tancowny, Jerry Hsu, Justin Figueroa, Kevin Long, Leo Romero, Marisa Dal Santo, Marquis Preston.

Modern Skateboarding: The Last Decade

The most recent era in skateboarding films is a testament to the evolution of the sport.

39. Zero – Cold War (2013)

Zero keeps the punk rock spirit alive with the Cold War video. Jamie Thomas still kills it in this video.

Featured Skaters: Ben Hatchell, Chris Cole, Dane Burman, James Brockman, Jamie Thomas, John Rattray, Nick Boserio, Tom Karangelov, Tommy Sandoval, Tony Cervantes.

40. Supreme – Cherry (2014)

Supreme’s Cherry is a full-length film since 1995. The video shows raw action, with new, current, and older skaters, setting a new standard for skate videos.

Featured Skaters: Too many to list.

Additional Skateboarding Classics

Here are some more videos that deserve a mention on the list.

41. CKY 2 (2000)

CKY 2 led to the Jackass series and the popularity of Bam Margera. This video is known for its crazy stunts and antics.

42. Santa Cruz – Wheels Of Fire (1987)

Wheels of Fire, from Santa Cruz, is a nostalgic video from 1987, which was the early era of skate videos.

43. Transworld – A Time To Shine (2006)

A Time to Shine is another video from Transworld, which is a great watch before a skate session.

Featured Skaters: Cooper Wilt, Paul Rodriguez, and many others.

44. ‘Baker’ Bootleg (1998)

This video is the beginning of awesome videos to come, showcasing the skating of Andrew Reynolds, Jim Greco, Brian Sumner, and Ali Boulala.

Featured Skaters: Andrew Reynolds, Jim Greco, Brian Sumner, Ali Boulala.

45. Vision – Psycho Skate

Psycho Skate shows the old school vert, freestyle, and street skating, with legends like Tony Hawk and Rodney Mullen.

Featured Skaters: Tony Hawk, Christian Hosoi, Rodney Mullen, Steve Rocco, He Who Shall Not Be Named, and many more.

46. Thrasher – Skate And Destroy (1996)

Skate and Destroy was released when skateboarding was becoming mainstream, which helped contribute to the new boom of skating.

Featured Skaters: Too many to list.

47. Foundation – That’s Life (2004)

That’s Life is a video full of hardcore skateboarding from the 2000s era.

Featured Skaters: Angel Ramirez, Corey Duffel, Daniel Shimizu, Ethan Fowler, Justin Strubing, Leo Romero, Matt Allen, Mike Rusczyk, Tony Silva, Gareth Stehr.

48. World Industries – Love Child (1992)

Love Child shows the skating of a young Daewon Song, along with other skaters, showcasing insane tricks and creativity.

Featured Skaters: Chico Brenes, Daniel Castillo, Spencer Fujimoto, Shiloh Greathouse, Daewon Song, Jovontae Turner, Randy Colvin, Jed Walters, Chris Branagh.

49. Zero – Dying To Live (2002)

Dying to Live is another video from the peak of skateboarding in the 2000s with legendary skaters like Chris Cole and Jamie Thomas.

Featured Skaters: Adrian Lopez, Chris Cole, Jamie Thomas, John Rattray, Jon Allie, Lindsey Robertson, Matt Mumford, Ryan Smith, Ryan Bobier.

50. Prime – Fight Fire With Fire (1994)

Fight Fire With Fire features some rad street skating and also the skating of Ben Pappas.

Featured Skaters: Al Boglio, Mike Crum, Caine Gayle, Chris Lambert, Kris Markovich, Jason Maxwell, Quy Nguyen, Shin Okada, Ben Pappas, Mike Santarossa.

51. Etnies – AB&A (2013)

AB&A is a video that took over a year to make, with spots from all over the world. It features skating by Axel Cruysberghs, Barney Page, and Albert Nyberg.

Featured Skaters: Axel Cruysberghs, Barney Page, Albert Nyberg.

52. All We Got Is Us (1990)

All We Got Is Us is a 1990s video from Chicago, featuring local skaters.

Conclusion

This list is a great resource for anyone who loves skateboarding or wants to learn more about the history of skate videos. Whether you’re a seasoned skater or just getting started, these videos are sure to inspire you to get out there and ride. Remember to support the skate community by buying videos when possible, and always keep pushing your limits and having fun.

For further exploration, check out these resources:

  • Best skateboard documentaries
  • Best skate video parts of the early 2000’s
  • skatevideosite.com

Ruben Vee, the author of the articleRuben Vee, the author of the article

By: Ruben Vee

Disclaimer: This article was created with the goal of informing readers about skate videos and was not created using any paid promotions. The content is based on an original post and has been formatted to improve readability.

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LongboardsGuide Team

Hi guys! We are LongboardsGuide team, welcome to our blog. We are here to help you choose the right gear to ride safely, together with Tom creating helpful tutorials and guides for beginners. Everyday I try to share my knowledge about it with all of you.