One of the greatest friendships in the Arrowverse has been the dynamic between Arrow’s Oliver Queen (Stephen Amell) and The Flash’s Barry Allen (Grant Gustin), ever since the Central City-based hero made his way into the Emerald Archer’s second season. Following Barry’s 2-episode arc in the second season, the first spinoff was created the night Barry was struck by lightning. Since then, the two heroes have essentially been the front and center of The CW’s DC TV line-up, primarily leading the crossovers where a trinity was eventually created when Supergirl (Melissa Benoist) came into the picture.

As the Green Arrow drama came to an end this season and Oliver’s big act in Crisis on Infinite Earths, the friendship between him and Oliver is one of the biggest losses in the Arrowverse. While they only got to share the screen once a year, the two heroes have always been a pleasure to watch whenever it’s time for the crossovers. Even though Barry has plenty of incredible dynamics still going on, his time with Oliver was still one of a kind. As Oliver’s time with the Arrowverse has ended, these are 10 of his best moments with Barry.

The Day They Met

The moment fans learned that a Flash TV show was happening and Gustin was cast in the role, a lot of anticipation was built up towards Oliver meeting the future hero. Arrow season 2 did a 2-parter to establish Barry before he headed into his own series. Even before he got his powers, it was made clear that he would become a major deal in what became later known as the Arrowverse.

Initially, Oliver was a bit apprehensive about Barry when he first visited Starling City. During the mysterious Mirakuru case, Barry was using this unusual case to explore the unexplained. With his mom having been mysteriously murdered by a man in yellow (Reverse-Flash): Barry was all about looking into special cases. While it didn’t start out on the best of notes, their first meeting was still a big moment. Barry being adorkable while Oliver, in his brooding way, was a bit taken back with this kid, was so enjoyable.

Oliver’s Mentorship Begins

Even before Barry suited up, he found a mentor in Oliver after having learned that he was the Arrow during his visit to Starling City. When The Flash first began, the pilot had a brief, but a powerful moment between Barry and Oliver as the soon-to-be Scarlet Speedster was trying to figure out what to do with his newly discovered powers. Oliver’s cameo in the series premiere was where his mentorship truly began as he gave Barry the inspirational speech he needed to officially use his speed for good.

Teaming Up Against Reverse-Flash

Despite having had a crossover earlier in the season, The Flash and Arrow fans got another mini-crossover between their respective seasons as the two heroes needed each other’s help. Towards the end of the spring season, the fastest man alive was in the midst of his battle with the Reverse-Flash (Tom Cavanagh) and got a few super-friends to help out.

For their penultimate showdown in the first season, Barry got the help of Firestorm (Robbie Amell) as well as Oliver (who was going by Al Sah-him temporarily) to take down Eobard Thawne. The trio working together to stop the villainous speedster was a good reminder of how fun crossovers can be as the franchise was expanding.

Becoming A Trinity With Supergirl

While the two heroes being the brave and the bold duo that they were was a lot of fun, it became even better once Kara entered the Arrowverse properly. During the Invasion crossover, Kara officially visits Earth-1 following her show’s move from CBS to The CW. Towards the end of the 4-show event, the trio officially became the DC TV trinity as Oliver and Kara had finally found an understanding for each other.

Oliver Supporting Barry After Flashpoint

Flashpoint was certainly one of Barry’s more controversial actions that played a large role in The Flash’s third season. With the time-travel action he had performed, it affected several corners of the Arrowverse, including John Diggle (David Ramsey) as his daughter Sara was replaced with John Jr. During the Invasion crossover, once everyone found out, almost everyone distanced themselves from Barry temporarily.

Oliver, however, didn’t as he, despite being new to the concept of time-travel, stood by Barry’s side. The speech he gives Barry in the time vault about how he’d have done the same for his dead parents if he had the power to change fate, was moving and incredibly human of him.

Reacting To Elseworlds

Elseworlds was Oliver’s penultimate, but perhaps craziest crossover he was ever put through, particularly with Barry. The event begins with Oliver and Barry swapping lives with Amell getting to play The Flash and Gustin playing the Green Arrow. To see the two actors swapping roles for this crossover was entertaining on several levels as were their characters’ reactions to the whole thing.

Training Each Other In Elseworlds

One of the funnier parts of Elseworlds was seeing Oliver and Barry having to train in how to be each other. With Barry being used to having powers, he had to learn some of Oliver’s more brutal methods.

For Oliver, he had to try and understand the complicated art of phasing that is harder than it sounds. But regardless, it was entertaining to see happen on screen as viewers never knew this would ever come to fruition where they swapped lives.

Barry’s Gift To Oliver

Oliver’s costume went through several evolutions throughout Arrow’s 8-year run. But something that was standing out in a bad way was his choice of a mask. The decision to have him use green greasepaint was an odd call that was, thankfully, abandoned thanks to Barry. Before returning to Central City, Barry left Oliver a simple, but useful gift that completed his Arrow look: a domino mask.

Flash Vs Arrow

Every dynamic duo has, at some point in their relationship, a showdown in one way or another. Barry and Oliver’s first crossover ended up having a battle as The Flash got temporarily affected by Rainbow Raider’s powers. While it’s certainly up for debate on who would have actually won, seeing them clashing demonstrated how The CW was fleshing out their DC Universe that now also included super-powers.

Their Final Scene Ever

One of the most tragic moments in the fourth hour of the Crisis crossover was Oliver’s second and final death. After he, as the powerful Spectre, had rebooted the universe, his final task in life was now complete. Even though his creation of Earth-Prime would bring back several deceased characters, Oliver’s death was permanent. Along with White Canary, Barry and Sara sit with Oliver in his final moments in life. Seeing Barry losing his mentor and closest friend, just like Sara, was devastating and pulled all the heartstrings in the most painful way.