Well, if you don't mind making a pact with some powerful entity, you could get 2 levels of warlock. This will give you access to a few spells, some of which perhaps being interesting (both stats and flavor-wise) for your character. But most of all, this will give you access to 2 invocations.
One of these invocations should be Devil's Sight, which grants you the ability to see through any form of darkness, magical or otherwise, for up to 120 feet. This is more than enough to cover the 15 feet of the darkness spell. Cast it on your clothes, and bring terror to your enemies.
While this is a good strategy (generally favored by blade pact warlocks), it has some limitations. While under the effect of the darkness spell, your allies cannot see you. As such, any spell requiring line of sight that they would like to cast on you simply cannot work. Healing you might be problematic, as it requires your allies to be able to touch you. They might know that you are smack in the middle of that sphere of pure black darkness but, once they get inside, it's suddenly not so easy to find you anymore.
These limitations also affect your enemies, however. Any attack from the outside of the sphere should have disadvantage as your enemies, even if they can approximate your position, can't exactly see you to aim properly. Enemies inside the darkness should also suffer from disadvantage when attacking you, unless they possess some form of blindsight or a similar ability. When you attack them, you should have advantage on the roll since you are functionally invisible for them.
The biggest cost of this strategy is the fact that it requires multi-classing. While the lvl 19 and 20 abilities for monk would not really be missed (realistically, few campaigns will reach these levels), it will still set you back 2 levels in obtaining you other core monk powers. Note that doing this would get you 2 invocations, however, and that some of them can be quite interesting for a ninja-esque character:
Armor of Shadows (cast mage armor at will, which might be better than
using your wisdom for AC if its under 16),
Eldritch Sight (cast detect magic at will),
- Eyes of the Runekeeper (allows you to read anything, even languages
you don't know... useful for spying!),
- Gaze of Two Minds (share the eyes of a willing target, more spying!),
- Mask of Many Faces (disguise self at will!), etc...
TL;DR
Sacrifice 2 monk levels and multiclass as a warlock. Gain some minor but potentially useful spellcasting, as well as the ability to see through magical darkness and one more ability of your choice!
No.
The cloud of Darkness would immediately snuff out the Light as soon as it was created. Note that the spell's text doesn't mention any restrictions or requirements involving which area effect, the Darkness or the Light, is created first. All that they need to do is overlap one another. If they overlap, even slightly, the Darkness instantly dispels the Light regardless of which was cast first.
The preferred spell to remove the entire cloud of Darkness is the 3rd-level evocation spell Daylight. However, theoretically, a 2nd-level Continual Flame spell cast with a 3rd-level spell slot could create light equivalent to a torch that would partially illuminate the Darkness but not permanently dispel it.
Entire description of Darkness (Player's Handbook, page 230):
Magical darkness spreads from a point you choose within range to fill a 15-foot-radius sphere for the duration. The darkness spreads around corners. A creature with darkvision can’t see through this darkness, and nonmagical light can’t illuminate it. If the point you choose is on an object you are holding or one that isn’t being worn or carried, the darkness emanates from the object and moves with it. Completely covering the source of the darkness with an opaque object, such as a bowl or a helm, blocks the darkness. If any of this spell’s area overlaps with an area of light created by a spell of 2nd level or lower, the spell that created the light is dispelled.
Emphasis mine. The spell's text implies that while nonmagical light cannot illuminate the magical darkness, magical light powerful enough not to immediately fizzle out can and will at least partially illuminate the darkened area.
Best Answer
Only spells that produce an "area of light" are dispelled by Darkness: Flaming Sphere is dispelled but not Color Spray
Jeremy Crawford says " I would allow the darkness spell to dispel any spell of 2nd level or lower that explicitly produces light."
This is DM guidance, not RAW, but let's break down the implication of this. There are four categories of 2nd level and under spell effects that mention light:
Spells that Describe an Area of Light
All of these spells mention an ongoing area of light produced by their effect. I believe there is a strong case to be made for darkness dispelling these spells. The text of the spell reads "If any of this spell's area overlaps with an area of light created by a spell of 2nd level or lower, the spell that created the light is dispelled". All of the above spells create "area of light". If we are to give any effect to this text, it must apply to these spells.
Spells with instantaneous effects that explicitly mention "light", but not an area of light
PHB page 203 states that instantaneous spells cannot be dispelled.
Spells with that explicitly mention "light" that vanishes quickly and is not in an area
The text of these spells include the word "light", but perhaps more for flavor than as an enforceable description of an effect. After all, we might expect all spells (or at least the ones that involve fire) to produce light - the mention of light here could be incidental. For example, Guiding Bolt reads "A flash of light streaks toward a creature of your choice within range."
We can't automatically exclude these spells as with Ray of Frost, because although the light effect reads as if it's instantaneous, the spell's duration is 1 round. But this duration is surely describing the lingering effect of the spells, not the light produced when the spell was first cast. I would rule that the duration of the light in Color Spray and Guiding Bolt is the same as in Ray of Frost, and therefor not subject to dispel.
Further, the darkness spell does not mention being able to dispel any spell that "creates light" - it specifically mentions spells that create an "area of light". These spells do not create an area of light.
Spells with lingering effects that explicitly mention "light", but not an area of light
In addition to the light produced in casting, guiding bolt leaves a dim light on a target for 1 round. Unlike Faerie Fire, this light has no area of effect. This is an edge case.
In favor of darkness dispelling: dispels this because (a) it's an ongoing light effect and (b) the light is mechanically pertinent to the spell's effect on the target, in that it provides advantage on the next attack "thanks to the mystical dim light glittering on the target until then."
Against darkness dispelling: although the light is a persistent effect, this spell does not create an "area of light" as described in the darkness spell.