This short script uses TextBlob and WordNet to add random glosses to almost every word in a poem. The effect is of a very diligent but overzealous grad student.

unhelpful_gloss.py

#! /usr/bin/env python

from textblob import TextBlob, Word
import random, sys

file = sys.argv[1]

def gloss_line(line):
  line = TextBlob(line)
  glosses = []
  for word in line.words:
    defs = word.definitions
    if len(defs) > 0:
      glosses.append((word, random.choice(word.definitions)))
  return glosses

with open(file, 'r') as f:
  text = f.readlines()
  for i,line in enumerate(text):
    if i % 5 == 0:
      print line.strip(), i
    else:
      print line.strip()
  print
  print "Glosses"
  print
  for i,line in enumerate(text):
    for g in gloss_line(line):
      print i, g[0] + ': ' + g[1]
    print

Sample output from Milton's Nativity Ode:

On the morning of Christs Nativity. Compos'd 1629.

THis is the Month, and this the happy morn
Wherin the Son of Heav'ns eternal King,
Of wedded Maid, and Virgin Mother born, 5
Our great redemption from above did bring;
For so the holy sages once did sing.
That he our deadly forfeit should release,
And with his Father work us a perpetual peace.

Glosses

0 On: in a state required for something to function or be effective
0 morning: the earliest period
0 Christs: a teacher and prophet born in Bethlehem and active in Nazareth; his life and sermons form the basis for Christianity (circa 4 BC - AD 29)
0 Nativity: the theological doctrine that Jesus Christ had no human father; Christians believe that Jesus's birth fulfilled Old Testament prophecies and was attended by miracles; the Nativity is celebrated at Christmas

3 is: have an existence, be extant
3 Month: a time unit of approximately 30 days
3 happy: marked by good fortune
3 morn: the time period between dawn and noon

4 Son: a male human offspring
4 eternal: tiresomely long; seemingly without end
4 King: (chess) the weakest but the most important piece

5 wedded: having been taken in marriage
5 Maid: a female domestic
5 Virgin: the sixth sign of the zodiac; the sun is in this sign from about August 23 to September 22
5 Mother: a term of address for an elderly woman
5 born: put up with something or somebody unpleasant

6 great: of major significance or importance
6 redemption: the act of purchasing back something previously sold
6 above: in or to a place that is higher
6 did: give rise to; cause to happen or occur, not always intentionally
6 bring: be sold for a certain price

7 so: in truth (often tends to intensify)
7 holy: a sacred place of pilgrimage
7 sages: droop, sink, or settle from or as if from pressure or loss of tautness
7 once: at a previous time;
7 did: carry on or function
7 sing: divulge confidential information or secrets

8 he: a very light colorless element that is one of the six inert gasses; the most difficult gas to liquefy; occurs in economically extractable amounts in certain natural gases (as those found in Texas and Kansas)
8 deadly: (used as intensives) extremely
8 forfeit: the act of losing or surrendering something as a penalty for a mistake or fault or failure to perform etc.
8 release: (music) the act or manner of terminating a musical phrase or tone

9 Father: Father' is a term of address for priests in some churches (especially the Roman Catholic Church or the Orthodox Catholic Church);Padre' is frequently used in the military
9 work: applying the mind to learning and understanding a subject (especially by reading)
9 us: a heavy toxic silvery-white radioactive metallic element; occurs in many isotopes; used for nuclear fuels and nuclear weapons
9 a: the blood group whose red cells carry the A antigen
9 perpetual: continuing forever or indefinitely
9 peace: a treaty to cease hostilities