Lisa: The First

Lisa features a combination of turn-based role-playing game combat in a 2D side-scrolling overworld. Several of the game's characters, including the protagonist, Brad, are addicted to a drug named Joy. It is claimed in the game that Joy causes its users to "feel nothing", but drastically increases the power of attacking moves of the player's party members, though gives them serious withdrawals when unused. The overworld features an assortment of settlements with shops and bars, where potential party members can often be found.

The game includes thirty different possible companions, though all, except for Brad are susceptible to permanent death through either scripted events such as Russian Roulette or against certain enemies, who will occasionally use permanent-kill moves.

Both The Painful and The Joyful take place in a post-apocalyptic wasteland called Olathe. Once a normal town, following an unseen cataclysm known as "The Flash", all women have perished, and humanity of Olathe was left with no way to reproduce. Lawlessness ravages most of Olathe, although certain areas are overseen by warlords, the strongest of which is known as the "Rando Army": a group clad in navy blue and red clothing led the titular martial artist "Rando", who always wears a skull-shaped mask and speaks aloud exclusively to a single subordinate.

Many have resorted to Joy, a highly addictive drug spread by a gang leader named Buzzo, that makes people "feel nothing". Unbeknownst to its users, Joy was developed by a man named "Doctor Yado" who appears periodically throughout the game playing a trumpet in several areas. The drug was developed in partnership with the military prior to the events of the game to create super soldiers, though was deemed a failure: as, although effective, it eventually causes users to become deformed, mindless creatures known as Joy Mutants which are controlled exclusively by Yado himself.

Prior to Lisa: The Painful's development, developer Austin Jorgensen created his first game called Lisa (retroactively retitled Lisa: The First) that was released as freeware on October 9, 2012. It focuses on the relationship between the titular Lisa and her father Marty, both of whom appear within future instalments of the series. The First differs significantly from The Painful, featuring a much greater emphasis on exploration and horror.

The First has been described by Jorgensen as a "Yume Nikki ripoff", as it borrows significant influence from Yume Nikki in structure. Upon the 2014 game's release, both games received alternative names, Lisa: The First and Lisa: The Painful respectively, to distinguish them. According to Jorgensen, The First was inspired by an ex-girlfriend of his describing her experiences of abuse, with the recollection making him ponder over how memories can effect people.

According to the review aggregate website Metacritic, Lisa: The Painful received "generally favorable reviews". Zach Welhouse of RPGFan praised the gameplay, graphics, story and soundtrack, but had mixed opinions about the game's moral choices, commenting that they "aren't always organically integrated into the plot, but nevertheless make for memorable scenes". Gensuke Okamoto of Kotaku Japan commented on the game, saying "While there have been RPGs with dark and depressing storylines before, it's rare to come across a game that leaves you with such a sense of despair even after winning". Tom Bowen of Screen Rant called it "a charming and humorous game that tackles some fairly serious issues along the way", saying while it could be "depressing at times" it was ultimately a positive experience. Mark Sammut of the same site said it "pushes the RPG Maker engine to its limits and shows what's possible with [the] tool with a lot of creativity", commenting on "the sheer amount of love present in the game" as a reason for its success.