Proeski sang for Macedonia in the 2004 Eurovision Song Contest and won many awards in former Yugoslavia.
Police said the 26-year-old's car was in a collision with a lorry on a motorway near the eastern Croatian town of Nova Gradiska.
In the Macedonian capital Skopje people wept in the streets. A day of national mourning will be held on Wednesday.
Local radio stations started playing Proeski's songs back-to-back.
"Macedonia and the Balkans lost an angel," said the head of the Macedonian Orthodox Church, Archbishop Stefan.
Two other people in Proeski's car were injured.
Proeski started his career aged 15, releasing his first album at 18.
| HAVE YOUR SAY I'm in shock. Macedonia has lost its greatest cultural ambassador Vojo Mihajloski, Tetovo, Macedonia |
Among Proeski's hits were Cija Si (Whose Are You?) and Ako me poglednes vo oci (If You Look Me In The Eyes).
He sang both in Macedonian and in Serbian and was seen as a bridge between people in a region often divided by ethnic hatreds, correspondents say.
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