How we cite our quotes: (Line)
Quote #1
When in disgrace with fortune and men's eyes, (1)
As usual, there are a few different ways to interpret Shakespeare's use of the term "fortune." A lot of readers scan this line and just assume the speaker is just down on his luck in general (out of favor with the goddess Fortune, a.k.a. fate). In other words, nothing's going this guy's way. That seems true enough, but we think the line holds another meaning as well. The word "fortune" can also mean "wealth" or "riches," so the speaker might also be hinting that he's down on his financial luck.
Quote #2
And trouble deaf heav'n with my bootless cries, (3)
Okay. "Bootless" literally means useless, so, on the one hand, the speaker is saying that his prayers feel like a waste of time because God doesn't answer them. But, at the same time, the use of the word "bootless" creates an image of poverty—as if the speaker is literally some kind of bootless (shoeless) beggar who is being ignored by God. This reinforces the idea that the speaker is spiritually bankrupt.
Quote #3
Wishing me like to one more rich in hope, (5)
Once again, we have a line that can be read two different ways. On the one hand, the speaker says that he wishes he could be like someone who has a lot more hope (is richer in hope). But, the line can also mean that he wishes he had better prospects (more "hope") of becoming "rich" or wealthy. Shakespeare seems to be asking which kind of wealth is more important, don't you think?
Quote #4
Desiring this man's art (7)
Here, our speaker says he wishes he had some other guy's talent ("art"), which is why this line has led some readers to believe that the speaker of Sonnet 29 is a poet or playwright who has suffered from artistic rejection or failure and has had some kind of economic setback as a result. While we can't read this sonnet as an autobiographical record of Shakespeare's life, it's fair to say that Shakespeare knew a thing or two about being a "starving artist." Between 1592 and 1594, an outbreak of the plague closed down London theaters (Shakespeare's livelihood), which might have led him to start writing the sonnets. By the way, we know from Sonnet 18 that Shakespeare's speaker is in fact a poet, even though there's no real evidence of the speaker's profession in this particular sonnet.
Quote #5
For thy sweet love rememb'red such wealth brings,
That then I scorn to change my state with kings. (13-14)
What's this? The speaker wouldn't trade places with even the wealthiest or most successful men on earth?! What's changed? For the first part of this sonnet, the speaker has been not-so-subtly suggesting that he's 1) penniless and 2) really unhappy about being broke. But, here, the speaker decides that the "sweet love" of a friend is enough to make him feel like he's rich, even if he doesn't have any money. In other words, you're never really "poor" if you've got someone to love.