[2] Despite previous disappointments, Ploutarchos' love of music pushed him back into the business and just two years after his first performance, he started appearing at club Rodolfo, which was followed by appearances at bigger clubs such as Neraida, Fantasia, and Tonel where he collaborated with well-known laïka names such as Giannis Poulopoulos, Rita Sakellariou, Themis Adamantidis, as well as Contemporary laïka artists such as Stelios Rokkos and Giorgos Mazonakis.

[1] Around that time, he met Dimitris Kardatzis and Ilias Filippou who believed in his talent, and got him in touch with his first producer Girgos Makrakis, who is credited with inspiring his stage last name "Ploutarchos".

[1] In late 1998, Ploutarchos signed with Minos EMI and shortly after released his debut album titled Mono Esi (Only you), which received moderate success.

[1][3] A year later in 2001 he released his third album titled Mikres Fotografies (Small pictures), which sold over 150,000 units,[2] and included a number of songs written by himself.

[2] In 2002, he released his fourth studio album titled Den Einai O Erotas...Paidi Tis Logikis (Love is not....a child of logic) which was later re-released in 2003 with the inclusion of bonus tracks and a DVD.

[2] Upon return to Greece, he released his sixth studio album titled Ola Se Sena Ta Vrika (I've found it all in you), which was a commercial success.

[2] On 18 September 2006, he released his seventh studio album titled Krimmena Mistika (Hidden secrets), which sold more than 40,000 units and was certified Platinum in its first week.

[5][6] The album was also released in a special edition form with the inclusion of a bonus DVD, while few days later on 20 September, Ploutarchos began appearances at club Kentro Athinon.

[10] Upon his return to Greece, Ploutarchos started appearing in a concert series at club Kentro Athinon alongside Apostolia Zoi, Tamta and Giannis Vardis on 25 October.

[9] In June 2008, Ploutarchos released his eight studio album titled O,ti Gennietai Stin Psihi (Whatever is born in the soul),[11] which was also certified 2× platinum.

[20] On 6 February 2011, Ploutarchos released a joint album with Al Bano Carrisi titled Dio Fones-Mia Psihi (Two Voices-One Soul) in Greece as a covermount with Proto Thema.

[21] On 17 February 2011, Ploutarchos took part in the Sanremo Music Festival alongside Albano Carrisi and Greek operatic soprano Dimitra Theodossiou.