Klingemann taught himself programming in the early 1980s. He then worked through advertising, design and motion graphics, as a junior copywriter, an intern at the London studio tomato, and a maker of techno flyers and TV title sequences, before co-founding the Munich media-art collective coma]² in 1997 and later the Munich FabLab.² One recurring technique, Neural Glitch, manipulates the trained weights of a generative adversarial network by randomly altering, deleting or exchanging them, producing misreadings of the input data that Klingemann has described as glimpses of autonomous creativity. Memories of Passersby I generates an endless stream of portraits in real time from inside an antique-looking cabinet. Because the piece is understood as the code and system rather than any single image, its sale at Sotheby's in March 2019 became one of the first times an AI artwork entered a traditional auction house.³

Klingemann was an early presence on Hic et Nunc, minting under the Quasimondo name and releasing This is Not a Code of Conduct v1.0, a work that helped set out an ethical framework for the platform's community.⁴ From 2016 to 2018 he was an artist in residence at the Google Arts & Culture Lab, and helped institutions including the British Library, Cardiff University and the New York Public Library process and classify their digital archives. Klingemann has also received the British Library Labs Artistic Award in 2016, the Lumen Prize Gold in 2018 for The Butcher's Son, and an honorary mention at Prix Ars Electronica in 2020 for Appropriate Response.² In Appropriate Response, visitors kneel on a prie-dieu before a split-flap display that uses AI to generate aphorisms, each one collectible as an NFT.⁵

Klingemann initiated Botto in 2021^6,7 as a social sculpture following the success of his earlier work Circuit Training, 2019.⁸ Botto was co-conceived with ElevenYellow and is governed by BottoDAO.⁶ Its direction is steered by weekly votes from thousands of DAO members, and its selected works are minted and sold to fund Botto's own development.^6,7 During Gallery Weekend Berlin in 2026, the solo show “Conflict of Interest” at SLEEK Art Space, curated by Anika Meier,⁹ presented new work made from a stated exhaustion with image-making, an attempt, in Klingemann's words, to go where it hurts rather than chase novelty.¹⁰