Arguably one of the most stacked up teams in skateboarding, Real Skateboards dropped their new video “OVAL” on November 8th, 2025. Featuring skaters like Mason Silva, Patrick Praman, Toby Ryan, and Ishod Wair, there is no shortage of talent on this squad. After watching the video, I thought it would be a fun idea to compare footage from two generations of skaters, Toby Ryan and Ishod Wair.
When thinking of how to choose a winner, it’s important to acknowledge that there are some incomparable aspects to their skating. It’s challenging to devise an objective method for rating two distinctly different approaches to street skating. That being said, I came up with several categories to rate them from which include technicality, risk factor, and overall impression. Each category will receive points out of ten based on my opinion, and whoever scores the most overall points will be deemed the winner.
Background
I have watched a lot of footage from both of these skaters over the years and am a fan of them. At 34 years old, Ishod Wair, originating from Bordentown, New Jersey, has been a household name for years. He has been in numerous video parts and has cemented himself as one of the best street skaters. Known for his extremely smooth style and high amount of technical ability, it’s not hard to see why he won Skater of the Year in 2013. Ishod has a polished, thought-out characteristic to his skating that can only be attained through years of experience.
On the other hand, fresh talent Toby Ryan is 22 years old and comes from San Marcos, California. Toby was picked by Ishod to join the Real team in 2024, making him one of the newest members of the squad. He has garnered attention from his impressive gap skating and the huge pop he has on the board. Toby has also participated in several skate contests, including Tampa AM and the new PSL skateboarding league. His debut part with Real and subsequent Venture Trucks release have cemented him as one of the most promising up-and-coming skaters of his generation. Although he lacks the experience and time on the board that Ishod has, he makes up for it with his risk-taking ability and raw commitment.
Technicality | Ishod – 9.1/10 | Toby – 6.6/10 |
After reviewing each of their clips, it is clear that Ishod is the leader in terms of technical skating. He has far more variation in his stance, more advanced grinds, and hard manuals that add a lot of elements to his footage. It is hard to pick clips of his to focus on because the level is incredibly high in all of them.
To start, at 21:09, he whips a nollie inward heel into a nose manual straight into a busy street. Considering the difficulty of the trick itself and the difficulty of the spot, this was a strong way to begin his part. Ishod also makes use of “mirror lines,” or lines that contain the same tricks but in different stances. For me, this always adds points because it shows variety and consistency.
Toby also had some technical skating, showing off some great switch ability in several clips. His most notable clip in this category was undoubtedly at 29:27. First, he rolls down a five-stair switch while maintaining the switch flip setup and keeping his shoulders straight. Then, he launches a huge switch flip down a famous NYC set, tweaking his feet to an intense degree. Not only was this an NBD, but an absolute gem of a trick to end his part off with.
Even though Toby had some technical moments in his part, he lost a lot of points due to the lack of lines. Ishod had several mind-blowing lines throughout his part. Many of these lines included flip-ins and included tricks that many pros couldn’t copy if they tried.
Risk Factor | Ishod – 7/10 | Toby – 9.5/10 |
Skating is already an inherently risky activity, but Toby truly takes it to the next level. Almost every trick in his section was done on a massive obstacle that included several dangerous elements. This is most clear at 25:04, where, after a kickflip into a steep hill, Toby gets annihilated on a telephone pole. This slam sets the tone for his part and highlights the fatal risks he’s taking for all of these tricks.
The first trick I chose to highlight for Toby is at 27:03, where he over-rotates a front 180 over and into a switch crook. Not only was he already flying at a hefty rail, but he did a trick that required him to do a full 180 over the rail. However, the clip that caught my eye the most was Toby’s ollie at 27:21. In order not to hit the cement walls at his sides, he had to aim his trajectory with absolute precision. This is one of those tricks where there aren’t good options to bail; you either commit or you don’t. You can see how he has to keep a tight form with his arms held close in order not to scrape his arms.
Although Ishod’s skating in this part wasn’t a walk in the park, he kept it pretty formulaic as far as gap skating. He hits a few decent-sized sets and gaps, showing off his signature front 180 flip tricks. The gnarliest trick during his part was the varial heel done at 20:10 down a massive double set. Overall, in terms of risk, Ishod kept it casual for his part, which will dock him some points in this category.
Overall Impression | Ishod – 8.5 | Toby – 8.9 |
As a whole, this video shows a snapshot of where both of these skaters are in their careers. Ishod has had the time to nail his style and form his extensive bag of signature tricks. Toby, an up-and-coming AM, has some great tricks but still has to find what his flow is. This being said, my overall impression of Toby is higher than Ishod’s because of the improvement from his previous video parts. In this new part, he does tricks I’ve never seen from him and hits uniquely death-defying obstacles. Ishod came out with his unarguable skill and finesse he has on the board, but didn’t appear to have the same hunger to improve that Toby does.
All things said and done, Ishod received a 24.6 and Toby ended with a 25. Both skaters had excellent footage with almost no filler. This was a pleasure to watch and review, and as a video, Oval is extremely strong. Watch it here.
