Machairitsas was born in Volos and began taking piano lessons at the age of six. These lessons lasted a year. At the age of nine he bought his first record, Help! by the Beatles. Three years later, he discovered Revolver by the Beatles.
His first job was at a record store, but because of his lack of punctuality he was fired. He disliked school, and after he started a fight with one of his teachers, he was expelled and excluded from all high schools. He went through countless jobs and served in the army for 14 months.
When he left the army, he started singing with Panos Tzabelas in Syntrofia. At the age of 20 he (as Larry), Pavlos Kirkilis (Paul), Takis Bassalakis (Jimmy), and Antonis Mitzelos formed a band called P.L.J. They moved to Paris, hoping for a musical career outside Greece. In 1982, their first album, Armageddon, produced by Giannis Doulamis, was released by PolyGram. At the time, the style of rock employed in Armageddon was not very popular, but it is now well thought of.
For their second album, they changed their name to Termites and started singing in Greek. In 1984, their third record had a positive reception, and they began gaining in popularity. Giorgos Ntalaras is also featured in this album. In 1986 they released their fourth album. The last studio record from Termites was "Perimenontas Tin Vrochi" (Waiting For the Rain), released in 1988.
Machairitsas began his solo career in 1989 as a writer and performer. His first album was O Magapas Kai I Sagapo, released by Minos-EMI. In 1991 he released Didymoteicho Blues, which was certified Gold.
Rixe Kokkino Stin Nichta was released in 1993 and featured many other artists. Since then he has been working closely with Dionysis Tsaknis, another well known Greek musician. Almost all their live appearances are made together. Their live performances have also been made into records.
In 1995, he released Parathyra Pou Kourase I Thea, considered by many to be his best album yet. In 1996, he released Pafsilypon with many other artists. Three years later, he released Etsi Drapetevo Ap' Tis Parees, again with many well-known musicians, especially in the song "Kai Ti Zitao". He then composed the music for the movie Enas Kai Enas. In 2001 he released To Dialeimma Krataei Dyo Zoes, which included songs such as "Matia Dihos Logiki", "Ela Psihoula Mou" and "O Egokentrikos". In 2002 he wrote the music for Giannis Kotsiras' album Xylino Alogaki. His next release was the two-disk album Tosa Chronia Mia Anasa (2007). It included a new song (the title song) and 34 of his career's greatest hits, being his first "best of" album.
Besides the many albums, Machairitsas and Tsaknis hold many concerts all over Greece during the summer. He has also held concerts with Eleftheria Arvanitaki, Haris Alexiou, Vasilis Papakonstantinou, Pyx Lax, Christos Thivaios and many more
Machairitsas continues to work in Greek rock music and to compose.
In 2016, Machairitsas performed at the Kaye Playhouse at Hunter College in New York during AKTINA's Greek Music Journey concert series.