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The first official lessfest followed initial test events, originally created as a joke to replicate a festival atmosphere for Vyzer’s "Aga Boo Waga" music video. However, it quickly became clear that the format could work for future virtual festivals, leading to the birth of lessfest. Coincidentally, Bishu was planning MOREFEST at the time, inspiring the name "lessfest" as a comedic counter to that. The entire lighting system was controlled via a keyboard and MIDI controller, directly hooked into Unreal Engine.

With Halloween approaching, lessfest 2 embraced a spooky theme, complemented by merch designs from Beans. This event expanded the festival’s universe and lineup while introducing Twitch chat integration—audience members could interact via virtual zombies in the crowd. A raid by Eliminate, thanks to bash explode, added to the excitement. The lighting system saw improvements, with some automation introduced, though much of it still relied on manual controls.

lessfest 3 was a non-canon "Christmas special" designed to celebrate the year’s end with a more relaxed atmosphere. Unlike previous editions, it was hosted in VRChat rather than Unreal Engine, using VRSL prefabs for the lighting system.

The most polished lessfest to date, lessfest 4 had a Moai/Easter Island theme, fitting for its Easter season debut. The event continued to expand its artist lineup and featured several technical improvements, particularly in lighting automation and optimization—though some elements still required manual control.

lessfest 5 shifted toward a warehouse-style aesthetic and introduced larger artists, such as Tails. The focus was on lighting advancements, marking the first use of DMX lights. Due to performance concerns, direct crowd interaction was removed.

The largest lessfest to date, in terms of crowd, featuring the biggest stage yet, complete with moving elements above the crowd. It maintained a Halloween theme but had a smaller artist roster compared to the previous year. Behind the scenes, technical stuff included playing video inside Unreal Engine without NDI, as well as nanite skeletal meshes for increased crowd density. However, crowd interaction from previous events (2 and 4) was not reinstated. Also, Bishu raided.

Similar to the previous year, lessfest 7 was a "Christmas special" with a smaller, cozier atmosphere. It reintroduced crowd interaction, testing new audience engagement features—such as spawning flying gift boxes when viewers gifted subscriptions.

This lessfest returned to a more typical setup where the fest venue was on top of a cruise ship.