Simulcasts have become the primary way that anime viewers are consuming anime, and are available on such services as Crunchyroll, FunimationNow, and HIDIVE, to name a few. From what I can tell, it appears that the first simulcast took place in Spring 2008, when Crunchyroll provided a simulcast of The Tower of Druaga ~Aegis of Uruk~.
Unfortunately, there were some stumbling blocks in the early days of simulcasting. For example, in May 2009, FUNimation Entertainment was going to provide the first simulcast of an episode of One Piece. However, a hacker had managed to find the episode on FUNimation’s server and made the episode available on the Internet the day before it was going to air on Japanese television. Due to this fiasco, FUNimation had to cancel the One Piece simulcast. However, the company was able to resume the simulcast three months later with the blessing of Toei Animation.
The next major stumbling block for simulcasting happened in October 2010, when Anime News Network would provide the site’s first ever simulcast, with the series Oriemo. Unfortunately, a hacker managed to exploit failures in a security system of a server contracted by ANN to host the videos. The thief downloaded the video and made it available on the Internet. Because of this incident, ANN had to temporarily suspend the simulcasts for both Oriemo and togainu no chi ~Bloody Curs~. Luckily, ANN was able to work things out to be able to resume the simulcasts of both series.
In January 2010, FUNimation began a simulcast for the anime series, Fractale. However, after the first episode was simulcast, the Fractale Production Committee halted the simulcast. The committee requested that FUNimation eliminate unauthorized videos of the episode that were made available on the Internet. While it’s never been explained how the episode became available outside of FUNimation, it’s been presumed that a streamripper (a program that can capture streaming video) was used to grab the episode, and then it was made available. FUNimation managed to do enough to quell the committee, so that the simulcast was able to resume.
After these initial stumbling blocks, simulcasting started to find its footing. Over time, more and more seasonal anime began being simulcast on various services, which led to the simulcasting structure that we are familiar with today. Looking back at the stumbling blocks, the infrastructure, and the players in early anime simulcasts, you realize just how far the concept of simulcasting has come over the past decade. While there may still be occasional issues with simulcasts, at least we’re not seeing the fiascos and stumbling blocks that were encountered during the early days.