1587:

Shakespeare is 23. (The last of his three children, twins Hamnet and Judith, were baptized 2 February 1585. I'm guessing that Shakespeare had already made his way to London by 1587, because by 1591 he has acted in plays and written some.)

London is a large and exciting place; its population is about 150,000, approximately 100 times that of Stratford. (By the year of Shakespeare's death it will be even bigger & more spectacular.)

Playhouses are flourishing: Both The Theatre and The Curtain are in operation, and the Rose Theatre is being built.

The Elizabethan Playhouses were all built on the same plan, a plan which made them a place to see and be seen, and excellent actors' theaters. See the Wikipedia page on the Globe.

Christopher Marlowe's Tamburlaine is performed and is an immediate hit.

What is beauty, saith my sufferings, then?
If all the pens that ever poets held
Had fed the feeling of their masters' thoughts,
And every sweetness that inspir'd their hearts,
Their minds, and muses on admired themes;
If all the heavenly quintessence they still
From their immortal flowers of poesy,
Wherein, as in a mirror, we perceive
The highest reaches of a human wit;
If these had made one poem's period,
And all combin'd in beauty's worthiness,
Yet should there hover in their restless heads
One thought, one grace, one wonder, at the least,
Which into words no virtue can digest.

England is engaged in an epic struggle with Spain: Mary, Queen of Scots, is executed.

1588 (William Shakespeare's Age = 24):

Defeat of the Spanish Armada, which was an existential threat to England.

Thomas Kyd's The Spanish Tragedy, or Hieronimo is Mad Again is performed and is a huge hit.

[ACT III. SCENE 2.]
[Spain: near the DUKE's castle.]
Enter HIERONIMO.

HIERO. Oh eies! no eies but fountains fraught with teares;
Oh life! no life, but liuely fourme of death;
Oh world! no world, but masse of publique wrongs,
Confusde and filde with murder and misdeeds;
Oh sacred heauens, if this vnhallowed deed,
If this inhumane and barberous attempt,
If this incomparable murder thus
Of mine, but now no more my sonne
Shall pass vnreueald and vnreuenged passe,
How should we tearme your dealings to be iust,
If you vniustly deale with those that in your iustice trust?
The night, sad secretary to my mones,
With direfull visions wake my vexed soule,
And with the wounds of my distresfull sonne
Solicite me for notice of his death;
The ougly feends do sally forth of hell,
And frame my hart with fierce inflamed thoughts;
The cloudie day my discontents records,
Early begins to regester my dreames
And driue me forth to seeke the murtherer.
Eies, life, world, heauens, hel, night and day,
See, search, show, send, some man, some meane, that may!

Publication of The Repentance of Robert Greene, Master of Arts and Greene's Groatsworth of Wit, bought with a million Repentance. Describing the folly of youth, the falsehood of make-shift flatterers, the misery of the negligent, and mischiefs of deceiving Courtesans. Written before his death and published at his dying request. Greene warns his fellow playwrights that there is "an upstart crow, beautified with our feathers, that with his tiger's heart wrapped in a player's hide supposes he is as well able to bombast out a blank verse as the best of you; and, being an absolute Johannes Factotum, is in his own conceit the only Shake-scene in a country." The allusion is to the Duke of York's denunciation of Queen Margaret:

O tiger's heart wrapt in a woman's hide!
How couldst thou drain the life-blood of the child,
To bid the father wipe his eyes withal,
And yet be seen to bear a woman's face?
3 Henry VI, 1.4.137-140.

Performance of Shakespeare's first tragedy, Titus Andronicus.