I've been a reddit lurker for 5 years or so. Around 2015 I began doodling cartoons as real-time responses to comments on threads. The doodles are usually relevant witty replies to the conversation and are either directly related to the parent comment or to the OP (Original Post). Here is the first time I pulled this off back in the League of Legends subreddit in 2015:
https://www.reddit.com/r/leagueoflegends/comments/3gw5gx/why_is_warwicks_q_a_spin_attack_when_the_tooltip/cu24xaf/?context=3
My first reddit doodle was a response to a meta question posted in the League of Legends subreddit /r/leagueoflegends.
I could probably write a whole guide on my methodology and how I make a specific cartoon land well with the intended audience. There's a fair bit of luck involved obviously (timing is everything on reddit) but a lot of it is also strategic and then simply being able to execute it in a short window of opportunity. For me personally, I have a knack of being able to draw cartoons rather quickly, I spend roughly 10 minutes tops on most of these which can lead to a rabbit hole of stupidity when I begin to reply to other users in real-time with additional cartoons. See below:
One of my personal favorite responses to one of my doodles was an accusation that I wasn't actually drawing these and simply signing my name on stolen content. I replied back to the user with this doodle. Check out the original comment here: https://www.reddit.com/r/leagueoflegends/comments/43p2id/jhin_is_available/czjxej8/
I do have my own style which I think contributes to the popularity of these throwaway doodles. The best way I can describe it is a juvenile affinity to dick jokes and Ren & Stimpy influenced vulgarity. I don't care though, I love it and I think it resonates with others. I've had success not just with the League of Legends crowd, but with the World of Warcraft sub, Overwatch sub and other smaller communities. Every so often I hit what I consider a perfect cartoon so I end up taking the original doodle as a draft and eventually flesh it out into an actual web comic. Here's is a notable example:
After this doodle struck a chord with the LoL community, that night I refined the concept even further and developed into a finished web comic. I posted it the next morning on the sub as a stand alone post and it ended up hitting the front page. Arbitraty internet points are fucking delicious.
This whole process is without a doubt one of my favorite things to do with my spare time. I've interacted with so many people over the last two years. Hundreds of thousands (maybe even millions) of redditors have laughed at my silly shit and I couldn't be happier. I've done hundreds of these yet few ever get to the popularity of the ones I've mentioned so far. Some of my personal favorites have been duds, killed by bad timing and remain buried in archived reddit threads to never be seen by anybody. As I mentioned before, luck is the single biggest factor that will determine success: The OP has to be no more than 2-3 hours old, one of the top 3 comments has to be something that you can draw a cartoon off and you have to be able to pull it off fast enough so that it doesn't end up getting buried below other comments, never to be seen. Besides luck, consistency is the next most important factor.
The payoff to these is anecdotal: reddit karma (which is rather useless) doesn't do much so it's difficult to translate the success of these into something more tangible. I've had a few people follow my other social media accounts as a result and grown my little fanbase somewhat but overall, these doodles have done nothing more than given strangers online a chuckle and most importantly, they've inspired me to create more. Maybe there's something in the equation I haven't cracked yet that will lead to bigger successes, but for now these remain largely a labor of love, and I'll keep on doodlin'.
Cheers,
ZOMBGiEF