Forget top ten lists, forget what you learned in that film course.  You may as well forget any notion of Unifying Themes.

Movies, film, cinema, videos, we watch them to be entertained, so let's agree to give up on an Objective Standard.

Instead, let me tell you about a month of movies you may enjoy.

On the First Day (or night), Annie Hall. If you start early enough, run it back to back with Manhattan. That will set a little tone for the month, and also get some of that seriousness out of the way. It will also establish you as a  person who appreciates  Black and White, Gershwin, and all of that stuff that ended up in ads for khaki pants later on.
On the second  night  A Mighty Wind, no BEST IN SHOW, no, WAITING FOR GUFFMAN. Heck, make it a saturday or sunday and you can watch all three.  You won't be disappointed.
On the third night,  Liquid Sky. Now there is some strangeness for you.
On the fourth night, White Mischief. A slightly different strangeness.
On the fifth, we risk a unifying theme by  going for a second Charles Dance film, PLENTY
On the sixth, we light LOCK STOCK AND TWO SMOKING BARRELS off of Sting's appearance in Plenty.
On the seventh, BUTCH CASSIDY AND THE SUNDANCE KID, followed by something else from either Newman or Redford,  say THREE DAYS OF THE CONDOR or  Cool Hand Luke or Cat on a Hot Tin Roof, but probably not THE STING.
On the eighth day, which is also Visitation day, THE STING, maybe followed up with TIME BANDITS
On the ninth night,  Metropolitan
On the tenth, MULHOLLAND DRIVE. If you are still in the mood to watch movies, try MULHOLLAND FALLS, just so you can explain the difference.
On the eleventh, SNATCH. It really is better than trying to do this back to back with Lock, Stock. You might also try  HEIST, which is a good introduction to David Mamet.
On the 12th, try STATE AND MAIN or THE SPANISH PRISONER, more from Mamet
On the lucky 13th, a little back- to- back: GLENGARRY GLEN ROSS and  HURLYBURLY, both adapted from plays
On the 14th The Grifters. For contrast, consider PRIZZI'S HONOR
On the 15th, SPITE AND MALICE, aka THE FORTUNE, and then, maybe BULWORTH
On the 16th POOTIE TANG and THE UNDERCOVER BROTHER
On the 17th MONTY PYTHON AND THE HOLY GRAIL, along with either THE MEANING OF LIFE  or LIFE OF BRYAN. Do not attempt all three. Remember Mr. Creosote.
On the 18th HOW TO MARRY A MILLIONAIRE, followed by THE MISFITS or SOME LIKE IT HOT, if you wish, or you can go back and try again with CAT ON A HOT TIN ROOF
On the 19th TO KILL A MOCKINGBIRD
On the 20th SOMETHING WILD. You don't want to be too sanctimonious for the upcoming visitation, do you?
On the 21st HIGH FIDELITY, maybe backed with GROSSE POINT BLANK
On the 22nd day, another visitation day: THE WIZARD OF OZ. Go ahead and write this down, so  you can discuss it with your ex later.  Flying monkeys are supposed to be scary. Sit down and watch the whole thing with your child.
On the 23rd, the original STAR WARS, or if you insist THE EMPIRE STRIKES BACK
On the 24th, SIX DEGREES OF SEPARATION, yet another adapted play
On the 25th, GOSFORD PARK. Be prepared to go back and try to catch the dialogue. You probably won't.. If you have any stamina left, try COLD COMFORT FARM.
On the 26th, try LOST IN TRANSLATION with BROKEN FLOWERS
On the 27th, GHOSTBUSTERS. Hey, you have a sense of humor and it's always good to see  Bill Murray from his original prime. Why not try ANIMAL HOUSE, too?
On the 28th,  Something with Spencer Tracy, maybe the original FATHER OF THE BRIDE or ADAM's RIB
On the 29th, THE PRINCESS BRIDE, which will send you scurrying for Wallace Shawn in SCENES FROM THE CLASS STRUGGLE IN BEVERLY HILLS.
On the 30th, go back and watch Manhattan again, then get out of the house for a while. You look a little pale.

Then try to figure out when you will watch these:
RONIN, Election, Town and Country, Something's Gotta Give, Chinatown, RIPLEY"S GAME, EASY RIDER, THE AMERICAN FRIEND, American Graffitti, Mrs. Parker and the Vicious Circle, GEORGIA, Le Divorce, Wild at Heart, Novocaine, Ramblin Rose, Apocalypse Now, the complete James Bond; Austin Powers, TAXI DRIVER,  etc.

A NOTE FROM WT: I have created another month-o-movies, which you may also enjoy, along with several other guides and reviews. Please check them out, too . And, if you have minute, how about a "helpfulness" vote for this one?

Thanks