As a singer he is first recorded in 1500 among the lay clerks at the funeral of Prince Edmund, the third son of Henry VII; he was also present at the funeral of Queen Elizabeth, wife of Henry VII, on February 23, 1503, Later lists place him at the head of the singingmen at the funeral of Henry VIl (May 11, 1509), the coronation of Henry VIII (June 24, 1509), the funeral of Prince Henry (February 27, 1511), and the great Anglo-French summit at the Field of the Cloth of Gold in the summer of 1520. Henry VIII, who was somewhat of a skilled musician himself, evidently admired Fayrfax's musical talents and granted the composer numerous royal benefices during the last few decades of his life. From 1509 he was awarded an annuity of £9 2s 6d on top of his salary as a Gentleman of the Chapel Royal.
Henry VIII made Fayrfax a Poor Knight of Windsor on September 10, 1514 to supplement his existing income; he received 12d a day for life. Henry continued to reward him by paying most handsomely each New Year's Day from 1516 to 1519 for books of music; in 1519 payment was for 'a ballad book limned' (that is, illuminated, or more probably simply copied), but the other sums for a 'book', 'a book of anthems' and a 'pricksong book' may have been for composition as well as copying. Fayrfax was paid enormous sums of money for music manuscripts, some amounting to £20. In June 1520, only a year before his death, Fayrfax once more headed the list of Gentlemen of the Chapel Royal when Henry went to France to meet Francis I at the Field of the Cloth of Gold.
From 1502 he may have been on the musical staff at the very rich St Alban's Abbey, though it is not known in what capacity. It has been suggested that Fayrfax was never likely to have been employed at St Alban's and probably held some sort of honorary post there; however, as he composed a mass and antiphon dedicated to St Alban and requested burial in the Abbey, a more substantial connection would seem once to have existed. Very little is known of Fayrfax's private life; a seventeenth-century rubbing of the monument brass which once marked his tomb in St Alban's Abbey reveals that he died on October 24, 1521 at the age of 57. He was survived by his wife, Agnes, and an unknown number of children.
Fayrfax may have been a composer of some national repute by his mid-thirties when a few of his compositions were copied into the Eton Choirbook (c.1500); Although Fayrfax, born in 1464, was therefore little over ten years younger than Browne and Lambe, only three of his surviving works were included in the Eton choirbook (Salve regina, Regali Magnificat, and Ave lumen gratiae). The Caius and Lambeth Choirbooks (assembled in the mid to late 1520s) contain the earliest surviving collections of his masses. Missa O quam glorifica is perhaps Fayrfax's most complex if not most impressive work. According to an inscription in the Lambeth Choirbook it was composed 'for his forme in proceading to bee Doctor'; no doubt this was his exercise for Cambridge University in 1504, the earliest English example known to us. The standard requirement for an early Tudor doctorate was the submission of a mass and antiphon, which were to be performed on the day of taking the degree (no antiphon of this type is known to have survived among Fayrfax's output).
Three of his works preserved in later sources (Aeterne laudis lilium,O quam glorificaand Lauda vivi Alpha et O) are known to have been composed as well as copied after c. 1500; probably a good number more are of similar date since, as we shall see in a moment, Fayrfax was very active musically in the first two decades of the sixteenth century. Aeterne laudis liliumis assumed from its words to be the antiphon in honour of the Virgin and St Elizabeth for which Queen Elizabeth of York paid Fayrfax twenty shillings at St Alban's in 1502: there is an obvious compliment to the Queen in the treatment of the name 'Elizabeth', because some voices sing this more than once despite the usual ban on verbal repetition, and because additional parts are specially introduced. Lauda vivi Alpha et Owas written in or after 1509 because it ends with a prayer for Henry VIIL
Fayrfax's surviving Masses, antiphons and Magnificats show that his reputation was well deserved. They are the work of an extremely thoughtful, discriminating composer who in particular achieved most subtle rhythmic effects very economically, and one who had little time for florid display. Even his scoring and textural schemes show restraint and economy: they are less obviously colourful than those of many Eton works, with for example no use of the gimel.
The decline in floridity is very important as one of the first marked signs of the sixteenth-century stylistic revolution. Crotchets are employed less, often much less, than before, and in particular the use of more than two or three in succession is now not common. Quavers, never frequent, appear scarcely at all, and triplet figures are virtually abandoned. There is even a tendency for minims to be used less freely and to attract syllables less often than in earlier music, even in sections with many syllables. All this might seem to imply just a total shift towards longer values and a quicker semibreve beat, but comparison of Fayrfax's notation as a whole with that of earlier men does not confirm this.