The crash involved a red Vauxhall Astra and a white Volvo lorry and happened around 5.20pm on the A92 Thornton bypass, between the Bankhead and Redhouse roundabouts.
The road was closed for a few hours while emergency services worked at the scene.
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Road Policing officers in Fife are now appealing for witnesses.
The 41-year-old man driving the Vauxhall was taken to Ninewells Hospital, where he is being treated for life-threatening injuries.
Sergeant Ewan Pearce, from the Glenrothes Road Policing station, said: “We are asking for anyone who witnessed the crash, or was driving through the area around the time, to come forward with any information they have, which could help our enquiries.
“Anyone with information can contact Police Scotland on 101, quoting incident 2547 of 20 November.”
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