Every day, thousands of people across the country go about their day in anticipation, just waiting for their phone to ping. The second they hear that Discord notification sound—which could be at 5pm or 4am—they drop what they’re doing and scramble to get online in time to hear the words “Welcome, welcome, welcome!” It’s time for another one of Raina’s wildly unpredictable chess streams, where the 23-year-old comedian plays games that alternate between brilliance and blunder, tense strategy and good-natured buffoonery.

Thanks to his unique wit and personality, Raina has amassed a significant following of fans who will break into dance at the sound of Gaadiwala Aaya, and whose vocabulary consists of exclamations like “haggar OP” and “bawaseer”. But how does a comedian—one of the winners of the second season of Comicstaan along with Akash Gupta—become one of the country’s top streamers with one of the biggest chess channels on YouTube?

Raina first gained notoriety in the Indian streaming world when he started playing PUBG with Tanmay Bhat, who is one of the first and most successful comics to take advantage of the opportunity presented by live-streaming. Bhat’s fans quickly took to Raina’s silly humour and less-than-average gameplay. From getting knocked out by his own flare to knocking out his teammates with a grenade, to his love of gas cans, Raina gave us some of the most hysterical moments on Bhat’s stream. As the lockdown continued, Raina started streaming his own PUBG games, but he really hit his stride once he switched to the game he loved the most—chess.

Raina was taught the timeless strategy board game by his grandfather, whom he would visit in Delhi during the holidays. “I instantly took to the game and would look forward to visiting Delhi to play chess with my grandfather,” he says. “I slowly started getting better and winning some games.”

It also helped that his parents encouraged him to keep playing. “My father had bought a computer which came with chess preinstalled on it,” he remembers. “I had installed GTA Vice City which my father would get very upset seeing me play. So to keep him happy and to avoid studying I would play chess.”

When Raina did his first chess stream, 40 people logged on to watch. Today, his YouTube channel has over 500,000 subscribers, with around 25,000 people watching him play at any given moment. While much of this can be attributed to his hard-work and love for the game, Raina’s trump card is his quirky, borderline-juvenile sense of humour that transforms watching a game as serious and cerebral as chess into an endearing and eminently enjoyable experience. In an ambitious move, Raina also convinced some of the biggest names in chess and comedy (and more) to come join him for a game.

The first edition of Comedians on Board, a chess tournament he organised with some of the best comics from the Indian comedy scene (and Yahya Bootwala) compete against each other, was a smashing success and got others in the online chess world to sit up and take notice. His first international collaboration came with Antonia Radic, better known as Agadmator, who runs one of the most popular chess channels on YouTube and is celebrated by chess aficionados for his incisive analysis of landmark games.

“I have always watched [Agadmator’s] videos to understand chess games,” says Raina. “I’ve been a big fan and he’s also played a role in improving my understanding of the game. So when he came on stream and we beat him as a team, it was such a great feeling.”

Within a few short months, he had played with or against some of the finest chess players in the world. The list includes GM Vidit Gujrathi (India no.3), Adhiban Baskaran (India no.4), Anish Giri (World no.10), Teimour Radjabov (World no.9), former Grandmaster Judit Polgar, and former World Champions Vladimir Kramnik and Vishwanathan Anand. Raina’s chemistry and ability to make his guests feel at ease also paved the way for a number of surprise players on the stream, including some familiar names in Indian hip hop such as Raftaar, EPR, Kr$na and Seedhe Maut, and even Indian cricketer Yuzvendra Chahal. All these streams have that special Samay Raina touch of comedic chaos, thanks to the often ingenious variations of the game that they introduce, including ‘Hand and Brain’ (where one player decides which piece to move, and another team-mate decides where to move it) and ‘Dice Chess’ (where the roll of the die decides which piece can move).

But the most exciting guest Raina has hosted yet is current World Champion Magnus Carlsen. “Leading up to the stream with Agadmator, I had made a WhatsApp group with the comedians called ‘Road to Magnus’,” he says. “It was just a joke that we were making. But just six months later to have the World Champion on stream with us was unreal.”

Comedians On Board has become the marquee event on the Indian chess streaming calendar, with the third edition—held between 19-21 November—featuring Raina and his fellow comedians training under the likes of Gujrathi, International Master Soumya, Grandmaster Surya Shekhar Ganguly and International Master and Chessbase India founder Sagar Shah. With a meta-narrative straight out of the World Wrestling Entertainment playbook—including (probably) fake feuds, rap disses, and heel turns—the competition was intense, with Raina’s arch-rival Joel Dsouza taking the final honours. On average, over 50,000 people were tuned it any time to watch Dsouza and Raina battle it out along with Biswa Kalyan Rath, Rahul Subramanian, Zakir Khan, Abish Mathew, Kusha Kapila, Tanmay Bhat and many others.

Raina and friends have also used their popularity as an opportunity to teach young Indians about their beloved game. Along with Sagar Shah, the man behind India’s biggest chess website, they’ve created a 100-episode series called Improving Chess, which consists of daily chess lessons for comics and chess enthusiasts Raina, Rath, Vaibhav Sethia and Anirban Dasgupta. It’s as good an entry point into chess for beginners as any.

As we near the end of a year dominated by the pandemic and the lockdown, Raina is looking forward to getting back on stage. He’s leaving Mumbai for Pune soon, hoping to get some stage time at open mics in the hilly city. But he doesn’t see himself take time off from chess or  streaming anytime soon.

“I’m going to be streaming for a while now, because it will take time for things to get back to normal after this pandemic,” he says. “I’ve become comfortable doing it now and enjoy myself.”