20 movies of the last 20 years that have great musical numbers

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1.
Billy Madison (1995)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
In order to inherit his fed up father's hotel empire, an immature and lazy man must repeat grades 1-12 all over again. (89 mins.)
Director: Tamra Davis
“ do you have anymore gum? ” - estolick
 
2.
The 40-Year-Old Virgin (2005)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother. (116 mins.)
Director: Judd Apatow
“ let the sunshine. let the sunshine in ” - estolick
 
3.
Clerks II (2006)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A calamity at Dante and Randal's shops sends them looking for new horizons - but they ultimately settle at the fast food empire Mooby's. (97 mins.)
Director: Kevin Smith
“ sit down girl. i think i looooove you ” - estolick
 
4.
Not Another Teen Movie (2001)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
A sendup of all the teen movies that have accumulated in the past two decades. (89 mins.)
Director: Joel Gallen
“ so what if we have the same mother? tonight i'm gonna f#%* my brother ” - estolick
 
5.
Anchorman: The Legend of Ron Burgundy (2004)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Ron Burgundy is San Diego's top-rated newsman in the male-dominated broadcasting of the 1970s, but that's all about to change for Ron and his cronies when an ambitious woman is hired as a new anchor. (94 mins.)
Director: Adam McKay
“ gonna find my baby gonna hold her tight ” - estolick
 
6.
Orgazmo (1997)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Naive young Mormon Joe Young is recruited to act in porn movies. (94 mins.)
Director: Trey Parker
“ what makes a man is it the woman in his arms? ” - estolick
 
7.
Fun with Dick and Jane (2005)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
When an affluent couple lose all their money following a series of blunders, they turn to a life of crime to make ends meet. (90 mins.)
Director: Dean Parisot
“ i believe i can sly her i go through that open door ” - estolick
 
8.
The Wedding Singer (1998)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other. (95 mins.)
Director: Frank Coraci
“ i'll even let you hold the remote control ” - estolick
 
9.
Jersey Girl (2004)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
After his career is sidelined by an unexpected tragedy and a personal blowup, a single man must take care of his precocious daughter. (102 mins.)
Director: Kevin Smith
“ me heart's aflutter ” - estolick
 
10.
Surf Ninjas (1993)
    1 2 3 4 5 6 7 8 9 10 5.0/10 X  
Two boys learn from a mysterious warrior that they are the heirs to the throne of Patusan and set out to overthrow the current monarchy. (87 mins.)
Director: Neal Israel
“ you got me rocking and a rolling rocking and a reeling ” - estolick
 
11.
Fantastic Mr. Fox (2009)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
An urbane fox cannot resist returning to his farm raiding ways and then must help his community survive the farmers' retaliation. (87 mins.)
Director: Wes Anderson
“ it blew me away at the beginning when they are stealthing across the farm together set to the beach boys ” - estolick
 
12.
Teenage Mutant Ninja Turtles II: The Secret of the Ooze (1991)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
The Turtles and the Shredder battle once again, this time for the last canister of the ooze that created the Turtles, with which Shredder wants to unleash an army of new mutants. (88 mins.)
“ yo, it's a green machine. gonna rock the town without being seen ” - estolick
 
13.
Ella Enchanted (2004)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
Ella is under a spell to be constantly obedient, a fact she must hide from her new step-family in order to protect the prince of the land, her friend for whom she's falling. (96 mins.)
Director: Tommy O'Haver
“ the scene where the giants make her sing someone to love is one of my personal favorites. ” - estolick
 
14.
School of Rock (2003)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
After being kicked out of a rock band, Dewey Finn becomes a substitute teacher of a strict elementary private school, only to try and turn it into a rock band. (108 mins.)
“ the legend of the rent was way hardcore ” - estolick
 
15.
I Think I Love My Wife (2007)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
A married man who daydreams about being with other women finds his will and morals tested after he's visited by the ex-mistress of his old friend. (94 mins.)
Director: Chris Rock
“ a movie where the couple randomly breaks into song at the end to settle their differences? how nifty ” - estolick
 
16.
Punch-Drunk Love (2002)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A psychologically troubled novelty supplier is nudged towards a romance with an English woman, all the while being extorted by a phone-sex line run by a crooked mattress salesman, and purchasing stunning amounts of pudding. (95 mins.)
“ the "he needs me" sequence is incredible. just incredible. ” - estolick
 
17.
Music and Lyrics (2007)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A washed up singer is given a couple days to compose a chart-topping hit for an aspiring teen sensation. Though he's never written a decent lyric in his life, he sparks with an offbeat younger woman with a flair for words. (96 mins.)
Director: Marc Lawrence
“ i said i wasn't gonna lose my head and then POP goes my heart ” - estolick
 
18.
A Prairie Home Companion (2006)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A look at what goes on backstage during the last broadcast of America's most celebrated radio show, where singing cowboys Dusty and Lefty, a country music siren, and a host of others hold court. (105 mins.)
Director: Robert Altman
“ dirty jokes, man i love 'em ” - estolick
 
19.
The Big Lebowski (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it. (117 mins.)
Director: Joel Coen
“ see what condition my condition was in ” - estolick
 
20.
Magnolia (1999)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
An epic mosaic of interrelated characters in search of love, forgiveness, and meaning in the San Fernando Valley. (188 mins.)
“ the ammie mann sequence gets me every time ” - estolick