There have been many portraits purporting to be of William Shakespeare over the years.
Of these, there are two which are definitely identified to him, although both seem to be from posthumous descriptions:
1. The Droeshout portrait (c.1622 – eight years after Shakespeare’s death) is the engraved frontispiece of the First Folio. A poem in the First Folio, by contemporary playwright Ben Jonson, says it is a good likeness.
2. The bust on Shakespeare’s monument in Holy Trinity Church, Stratford-upon-Avon, erected within six years of Shakespeare’s death in 1616. This is thought to have been commissioned by Dr John Hall, the poet’s son-in-law. The face appears to be fairly generic, and does not give any great insight into the actual man himself.
With no definitive evidence that anyone ever commissioned a portrait of Shakespeare, we are currently left with three unattributed paintings (on our front page slide-show) which are within the realm of serious consideration:
The ‘Cobbe’ portrait (in the possession of the Cobbe family since the early 18th century) is said by the Shakespeare Birthplace Trust (in 2009) to be a portrait from life. It is hanging at Hatchlands Park in Surrey (National Trust). Several copies have been attributed to this original, suggesting that the sitter was a very well-known person.
In particular, it is believed that the Cobbe portrait was copied by another artist, resulting in the ‘Janssen’ portrait. Before 1988, this showed an older man with receding hairline, much like the Droeshout First Folio portrait. However, when this painting was cleaned of overpainting in 1988, a likeness similar to the ‘Cobbe’ was revealed. It is now believed that this cleaning removed an alteration that showed Shakespeare in his old age, although whether this alteration was before the First Folio engraving (above), or after it, is speculation. It is in the Folger Shakespeare Library, in Washington DC.
The ‘Chandos’ portrait (once in the possession of the Duke of Chandos, now at the National Portrait Gallery) is attributed to John Taylor, dated c. 1610. Tarnya Cooper (National Portrait Gallery; report 2006) states this is the only one that has a claim to have been done from real life. The Cobbe portrait (above) was ‘discovered’ later than this, but Cooper has since restated her opinion. It is in the National Portrait Gallery, London.
There are other portraits claimed to be done during Shakespeare’s lifetime, or soon after. None have the provenance of the ones mentioned above. There are many discussions about these other claimed portraits on various internet websites. An internet search of ‘Shakespeare portraits’ will give you many references to look at.