Hallfreor Óttarsson vandraeaskáld was one of the best known skalds in early medieval Iceland. Both his poetry and his adventurous life (especially his relations with the King of Norway Olav Tryggvason and his love affair with Kolfinna) ensured him a mention in several family sagas and the highest honour of all, a saga extolling his own deeds (Hallfreoar saga). His dealings with the jarls of Hlaoir and King Olav gained him the reputation of an important and reliable witness of Norway's turbulent politics at the turn of the 10th century. At any rote, his younger colleagues who sought to evoke in their sagas the reigns of jarl Hakon and Olav Tryggvason would treat Hallfreor's poems as a most authoritative source. The article focuses on two aspects of skald's biography, the nature of his relationship with the jarls of Hlaoir (Hakon and Erik) and Olav Tryggvason and the background of his conversion to Christianity. Hallfreor's own verses, which feature Hakon, Erik and Olav, as well as the subsequent saga narratives would have us believe that it was his poetic skill that made him a most welcome guest at the courts of Norway's rulers. The status of a highly-skilled poet may indeed have allowed Hallfreor to move freely between the rivalling parties and his current hosts to ignore his ties to their enemies. As far as the lausavisur which refer to his conversion are concerned Hallfreor's evident unease about that decision may be interpreted as a indication of the strength of the social and political pressures he was exposed to. He probably feared that by embracing Christianity he would lose his privileged status as a generally respected and independent skald. Hallfreor may well have anticipated that once he repudiated Odin and pledged his allegiance to Christ he would be obliged to serve the king and put his poetry at the disposal of royal will.