In 1571 Nicholas Hilliard (age 24) produced "a booke of portraitures" for Robert Dudley 1st Earl of Leicester (age 38).

In 1572 Nicholas Hilliard (age 25) painted the "Pelican Portrait" of Elizabeth I (age 38).

The Pelican being the pendant hung from her necklace of pearls; pearls a symbol of virginity. Pelicans traditionally used as sign of self-sacrifice since the Pelican was believed to peck at her own breast to feed her young; the symbolism meaning Elizabeth had sacrificed herself for England.

Other details include the highly decorated armlet above her elbow and many jewels over her red velvet gown and headress. The two cherries tucked into her right ear possibly refer to her virginity; possibly an over-interpretation of the modern use of cherry.

Research in 2010 found the painting used wood from the same tree used for the Phoenix Portrait.

In 1572 Nicholas Hilliard (age 25) painted the "Phoenix Portrait" of Elizabeth I (age 38).

Research in 2010 found the painting used wood from the same tree used for the Pelican Portrait.

In 1572 Nicholas Hilliard (age 25) became portrait painter to Elizabeth I (age 38).

Around 1574 Nicholas Hilliard (age 27) invested in a gold mine in Scotland. The venture failed. Hilliard's life was beset with money issues.

In 1576. After Nicholas Hilliard (age 29). Portrait of Mary Queen of Scots (age 33).

In 1576 Nicholas Hilliard (age 29) travelled to France where he stayed with the English Ambassdor to France Amyas Paulett.

In 1576 Nicholas Hilliard (age 29), whilst in France, painted a portrait of Francis Bacon 1st Viscount St Alban (age 14) who was attached to the English Embassy at the time.

1576. Nicholas Hilliard (age 29). Miniature Portrait of Charles Howard 1st Earl Nottingham (age 40).

On 05 May 1576 Nicholas Hilliard (age 29) was given the monopoly on producing miniatures and engravings of King James I of England and Ireland and VI of Scotland (age 9) by the King.

Around 1577 Nicholas Hilliard (age 30) painted a portrait of Amyas Paulett.

In 1577 Nicholas Hilliard (age 30) was provided with a stipend of 200 livres by Francis Valois Duke Anjou (age 21), a suitor of Elizabeth I (age 43).

Around 1585. Nicholas Hilliard (age 38). Miniature Portrait of Anthony Mildmay (age 35). Hilliard represents Mildmay standing in a luxurious tent filled with beautiful furniture preparing for a tournament surrounded by objects that allow the artist to feature a variety of rich textures including red velvet, blue ostrich feathers, and gleaming metal.

Around 1590 Nicholas Hilliard (age 43). Portrait of George Clifford 3rd Earl of Cumberland (age 31).

Around 1590 Nicholas Hilliard (age 43). Portrait of Mary Sidney Countess Pembroke (age 28).

Mary Sidney Countess Pembroke: On 27 Oct 1561 she was born to Henry Sidney and Mary Dudley. On 21 Apr 1577 Henry Herbert 2nd Earl Pembroke and she were married. She by marriage Countess Pembroke. The difference in their ages was 23 years. He the son of William Herbert 1st Earl Pembroke and Anne Parr Countess Pembroke. On 25 Sep 1621 Mary Sidney Countess Pembroke died of smallpox at Herbert Townhouse Aldersgate Street. Her funeral was held at St Paul's Cathedral. She was buried at Salisbury Cathedral.

In 1591 Nicholas Hilliard (age 44) painted a portrait of Francis Drake (age 51).

In 1591 Nicholas Hilliard (age 44) painted a portrait of Walter Raleigh (age 37).

Around 1592 Nicholas Hilliard (age 45) painted a portrait of Lettice Knollys Countess Essex (age 48).

In 1597 the John Donne (age 24) praised Nicholas Hilliard (age 50) in his poem "The Storm": A hand or an eye, By Hilliard drawn is worth an history, By a worse painter made.

In 1599 Nicholas Hilliard (age 52) secured an annual allowance from Elizabeth I (age 65) of £40.

Around 1600 Nicholas Hilliard (age 53) painted the portrait of King James I of England and Ireland and VI of Scotland (age 33).

Around 1600 Nicholas Hilliard (age 53) wrote his treaty on painting called "The Art of Limning".

In Jul 1601 Nicholas Hilliard (age 54) wrote to Robert Cecil 1st Earl Salisbury (age 38), asking permission to retire from London and live more cheaply in the countryside. He explained that he had trained apprentices who now competed with him in the private painting market. Hilliard asked that Cecil employ his son as a clerk, because he could not keep him in his own trade.

In 1617 Elizabeth I gave Nicholas Hilliard (age 70) £400 for having made a second Great Seal.

In 1617 Nicholas Hilliard (age 70) was briefly imprisoned in Ludgate Prison after standing surety for the debt of another, and being unable to produce the amount.

On 07 Jan 1619 Nicholas Hilliard (deceased) was buried in St Martin's in the Fields [Map]. In his will he left twenty shillings to the poor of the parish, thirty between his two sisters, some goods to his maidservant, and all the rest of his effects to his son, Lawrence Hilliard, his sole executor.