Thomas, and Alfred Soto and popmatters http://www.popmatters.com/pm/post/154220-the-top-15-madonna-singles-of-all-time/P1">put together lists of the best madonna songs

here is my top 20

20 American Pie- American life was mostly a weird concept album, marked by anxiety about her status, and concerns about her status as a performer, but the queer sadness of her version of this had a slippery profoundity.
19 Rainbow Tour--because her singing the line Christian Dior me, had a winking camp nod, against all of the pomp of Evita's vanity.
18 Breathless--Because it was done by Sondheim, and she understood the theatricality of what that implied.
17 Deeper and Deeper Dance as Sex, as Religion, and as Fame--with the Warhol aping video, and the half sheen groove,
16 Frozen Yeah, she was in the middle of a religious phase, but it is odd that she sounds so autobiographical, and on the edge of losing control. and just beautiful.
15 Cherish As sweet as she has ever been, and just this side of cute, given extra gravitas for it's doo wop heritage, and it's cribbing from the Assocation.
14 Papa Don't Preach Mostly for the autonomy
13 Into The Groove I like the studio as instrument in this one--the overdubs, the double tracking, sort of proto-autotune in its elegant artifice.
12 What it Feels Like for a Girl The closest she ever got to a country ballad, and something I want Gillian Welch to cover, windswept, loveley, and heart breaking.
11 Justify My Love Because it's hot and sexy and dykey and it reminds you of a time in the 90s when Judith Butler got you laid.
10 This Used to be my Playground The song about lost innoncence and childhood yearning that Michael Jackson tried to sing for a decade--the video is the first time i remember being transfixed by MTV (or the Canadian Equivalent)
9 Material Girl For the sung/spoken chorus
8 Like a Prayer---Holy. impure but holy
7 Die Another Day I love how it marshalled it's ambition, how it took over what it meant to be a bond song, and i love it's abstractions. Vastly under rated.
6 Dress You Up That typical 80s drum beat
5 Lucky Star Perhaps her best pure pop, 3 minutes, in and yr out, pop song. As good as anything by the Beatles.
4 Vogue The politics are complicated--but I think Madonna as a taste maker, and as a bricoluer are vastly under rated--this is amazing because of the vocals, because of the coldness of it, because of it's cleverness, and it's theatricality--sort of proves Madonna as both democratization and evangelical of queer art.
3 Hung Up Abba as history. Pop as a game of signifers. Fantastic video.
2 Holiday You are singing the chorus right now, admit it.
1 Le Isla Bonita Because it is so slight, so slippery, it might as well float away, and it almost does--transient in the best way.