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The Best Of: Madonna

Click the cover art for the music videos.

Originally posted in 2013. Updated in 2020.

Back in 2013, Madonna turned 55, and so I took the opportunity to count down my 55 favourite Madonna singles of all time — something you wouldn't be able to do for many other artists, since few have released that many singles let alone had 55 good ones in their career.

Spanning from 1982 to 2012, the list includes some songs that aren't considered Madonna classics, but is also missing others that are (sorry, "Justify My Love"). And although my ranking is now seven years old, nothing she has released in the years since I compiled this list has made the grade. On the one hand, that means I don't have to adjust it, but on the other, it's a shame I haven't really enjoyed her last couple of albums.

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Madonna: almost as many image changes as hit singles

Around the time I originally compiled my countdown, Billboard also released a list of Madonna's 40 most successful singles on the Hottest 100. "Like A Virgin" was crowned number 1, with Billboard's list based on chart performance (highest position, number of weeks on the chart, etc.) rather than straight sales or airplay tallies.


That song doesn't fare anywhere near as well on my list, which is based on my own preferences — a rather unscientific approach, I guess, but no one knows what I like more than me.

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55. This Used To Be My Playground

Year: 1992
Album: single only; later included on Something To Remember
Charts: #9 AU, #3 UK, #1 US

Released between the sexual onslaught of 1991's "Justify My Love" and 1992's Erotica, this demure ballad came from the soundtrack of baseball flick A League Of Their Own. Madonna also starred in the film, and I'd love to say something about her performance but I never did get round to seeing it.

Read more here.

54. Give Me All Your Luvin'

featuring Nicki Minaj & M.I.A.

Year: 2012
Album: MDNA
Charts: #25 AU, #37 UK, #10 US


It received plenty of publicity thanks to a certain Superbowl performance, but "Give Me All Your Luvin'" became Madge's most disappointing chart performance for an album's lead single since debut release "Everybody".

53. Take A Bow

Year: 1994
Album: Bedtime Stories
Charts: #15 AU, #16 UK, #1 US


A massive success in the US, where radio programmers liked Madonna most when she wasn't pushing the envelope, "Take A Bow" received a helping hand (and voice) from superstar producer Babyface. 

Read more here.

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52. Bye Bye Baby

Year: 1993
Album: Erotica
Charts: #15 AU


Only released in a handful of territories (Australia included), this sixth single from Erotica came with a cobbled-together clip featuring footage from The Girlie Show tour.

Read more here.

51. Keep It Together

Year: 1990
Album: Like A Prayer
Charts: #1 AU, #8 US


In the States, it was issued as a single in its own right, whereas in Australia it was released alongside "Vogue" — but either way, this became the sixth and final hit from Like A Prayer.

Read more here.

50. Like A Virgin

Year: 1984
Album: Like A Virgin
Charts: #1 AU, #3 UK, #1 US


The song that turned Madonna from a singer of a few catchy pop tunes into a global phenomenon has never been among my favourites, but there's no denying its place in music history.

Read more here.

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49. Ray Of Light

Year: 1998
Album: Ray Of Light
Charts: #6 AU, #2 UK, #5 US


Another song that other people seem to like a lot more than me, "Ray Of Light" is possibly the most critically acclaimed of all Madonna's hits and the first to win a Grammy (although she'd previously received an award for Best Long Form Music Video for Blonde Ambition World Tour Live).

48. Miles Away

Year: 2008
Album: Hard Candy
Charts: #39 UK


From one of Madonna's most polarising albums comes this track, which flew so under the radar that casual music fans probably wouldn't even have realised it was a single. The song's inspired by her relationship with former husband Guy Ritchie.

47. What It Feels Like
For A Girl

Year: 2001
Album: Music
Charts: #6 AU, #7 UK, #23 US


Teamed with her most controversial video in some time, this track taken from Music received a Perfecto makeover for the single release — although I've always preferred the more subdued album version, which you can listen to here.

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46. Everybody

Year: 1982
Album: Madonna
Charts: #107 US


The single that started it all. Well, it didn't really set the charts alight, but it was Madonna's debut release and still sounds as good today as it did back in the early '80s.

45. Rescue Me

Year: 1991
Album: The Immaculate Collection
Charts: #15 AU, #3 UK, #9 US


One of two new tracks recorded for Madonna's first greatest hits album, "Rescue Me" did pretty well considering it never had a video (not even a concert clip) available for music TV play.

Read more here.

44. Music

Year: 2000
Album: Music
#1 AU, #1 UK, #1 US


Madonna kicked off a new decade still on top of just about every major chart around the world and showed no signs of giving up her music crown any time soon with this title track from her eighth album another global smash. Then, "American Life" happened.

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43. Dear Jessie

Year: 1989
Album: Like A Prayer
Charts: #51 AU, #5 UK


Released in Britain instead of "Oh Father" (Australia got both singles), this cute track was accompanied by a music video which was the second in Madonna's career (after "Who's That Girl") to feature her in cartoon form. 

Read more here.

42. Rain

Year: 1993
Album: Erotica
Charts: #5 AU, #7 UK, #14 US


Even Madonna's most sexually charged album had a soft side — and this Erotica single proved she could still score a hit without relying on shock factor. In Australia, it returned her to the top 10 after a couple of under-performing singles.

Read more here.

41. Hollywood

Year: 2003
Album: American Life
Charts: #16 AU, #2 UK


Ten years after "Rain", the shock factor of Madonna kissing Britney Spears and Christina Aguilera did nothing to help this single crack the US chart, although that MTV performance probably helped its chart position elsewhere in the world.

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40. Don't Tell Me

Year: 2000
Album: Music
Charts: #7 AU, #4 UK, #4 US


Music's title track was the bigger hit, but I preferred this follow-up. And while not a global chart-topper, "Don't Tell Me" was still another smash — its number 4 peak in the US gave Madonna back-to-back top 10 hits there for the last time (to date). The song was written by her brother-in-law, Joe Henry (husband of sister Melanie), and adapted by Madonna and producer Mirwais Ahmadzaï.

39. The Power Of

Year: 1998
Album: Ray Of Light
Charts: #33 AU, #6 UK, #11 US


America sensibly skipped over "Drowned World (Substitute For Love)" and went straight onto this single after "Ray Of Light", whereas elsewhere "The Power Of Good-bye" was the fourth track lifted from Ray Of Light. Another ballad, the track's video took Madonna back to the beach for the first time since "Cherish" and featured ER star Goran Višnjić as her love interest/chess rival.

38. Get Together

Year: 2006
Album: Confessions On A Dance Floor
Charts: #13 AU, #7 UK, #106 US

Apparently released as Confessions' third single due to its high download tally, "Get Together" continued a trend that began with American Life of later singles failing to chart on Billboard's Hot 100. Elsewhere, it was a decent-sized hit, influenced by "Music Sounds Better With You" —  although not as heavily as "Hung Up" drew from ABBA, since the writers of the Stardust track did not receive a credit.

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37. Oh Father

Year: 1989
Album: Like A Prayer
Charts: #59 AU, #16 UK, #20 US


One of Madonna's most personal songs (dealing with her mother's death and father's remarriage) was the fourth single from Like A Prayer in the US. Quite a change of pace, it became her first single to miss the US top 10 since 1984's "Lucky Star". Finally released as a single in the UK in 1996 to promote ballads collection Something To Remember, it also missed the top 10 there.

Read more here.

36. Secret

Year: 1994
Album: Bedtime Stories
Charts: #5 AU, #5 UK, #3 US



Co-produced by Madonna and Dallas Austin, "Secret" marked a shift from pop and dance to R&B, the genre of choice for sixth studio album Bedtime Stories and one she'd return to 14 years later on Hard Candy. "Secret" is the highest ranking track from Bedtime Stories on this list, with other singles "Human Nature" and "Bedtime Stories" not making the cut.

Read more here.

35. Love Profusion

Year: 2003
Album: American Life
Charts: #25 AU, #11 UK



Issued in combination with "Nothing Fails" in some parts of the world, "Love Profusion" actually had a music video filmed for it and is, in my opinion, the better of the two songs, which were both released towards the end of 2003. In the US, both tracks followed the lead of "Hollywood" and gave the Hot 100 a wide berth.

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34. Nothing Really Matters

Year: 1999
Album: Ray Of Light
Charts: #15 AU, #7 UK, #93 US



The fifth and final single from Ray Of Light was given a great remix by Club 69 (which you can listen to here) and it's that version that's responsible for the song appearing so high on this list. Click the cover art for the video version, which features Madonna dancing around in a red kimono.

33. You'll See

Year: 1995
Album: Something To Remember
Charts: #9 AU, #5 UK, #6 US



By 1995, the world was ready for a break from the seemingly relentless shock and awe Madonna's career had offered up since "Like A Virgin" — and so, sensing the time was right for another image adjustment, this emotional ballad kicked off the Something To Remember campaign and set the stage for Evita to re-establish Madonna as a serious performer.

32. Angel

Year: 1985
Album: Like A Virgin
Charts: #1 AU, #5 UK, #5 US



Another track with an interesting history, "Angel" was teamed with Desperately Seeking Susan soundtrack hit "Into The Groove" (available on the 12") in Australia — and that double A-side topped the chart. In the US, the Hot 100 run of "Angel" was entirely down to that song, with "Into The Groove" only qualifying as an airplay hit. Meanwhile, in the UK both songs received separate releases.

Read more here.

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31. Celebration

Year: 2009
Album: Celebration
Charts: #40 AU, #3 UK, #71 US


One of two new tracks included on career retrospective double CD collection Celebration (an album which also marked the end of her relationship with Warner Music), this title track received a rather muted response from the record-buying public. I prefer the album version, which you can listen to here, while click the cover art for the video version.

30. True Blue

Year: 1986
Album: True Blue
Charts: #5 AU, #1 UK, #3 US



After "Hanky Panky", this is possibly the cheesiest single of Madonna's career — but unlike the Dick Track hit, "True Blue" is still one of my favourites. That said, it's the lowest-placed single from the album of the same name. Like a few Madonna songs, the best bit isn't the chorus, but the middle eight ("No-oh more sadness/I kiss it goodbye...), which we get to hear twice — another common feature.

Read more here.

29. Deeper And Deeper

Year: 1992
Album: Erotica
Charts: #11 AU, #6 UK, #7 US



I was never a fan of "Justify My Love" or "Erotica" (which both fail to register on this list), while "Rescue Me" and "This Used To Be My Playground" place quite low down, so by late 1992, I'd begun to fear Madonna might have lost her touch. Thankfully, this disco-infused second single from Erotica restored my faith.

Read more here.

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28. Spotlight

Year: 1987
Album: You Can Dance
Charts: #32 US (airplay chart)



A new song that appeared on remix album You Can Dance (after failing to make the cut for True Blue), "Spotlight" didn't received a full commercial release in most countries — but was issued as a single in Japan, and so it qualifies for this list. It also features another great middle eight: "This is your chance to shine/Don't be afraid to fall...".

27. Causing A Commotion

Year: 1987
Album: Who's That Girl soundtrack
Charts: #7 AU, #4 UK, #2 US



Despite being among her biggest hits of the '80s, "Causing A Commotion" has never appeared on any Madonna greatest hits collection — and didn't even receive a proper music video at the time. And, yep, once again the best bit is the middle eight: "I hope you find what you're looking for/Is it mine walk through that door..."

Read more here.

26. Die Another Day

Year: 2002
Album: American Life
Charts: #5 AU, #3 UK, #8 US



By 2002, there wasn't much Madonna hadn't done — so it seemed inevitable the responsibility of recording a James Bond theme song would eventually fall to her. Despite being the most successful theme since Duran Duran's "A View To A Kill", many critics weren't impressed. This critic was, although I agree her role in the film as a fencing instructor was unnecessary.

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25. 4 Minutes

featuring Justin Timberlake

Year: 2008
Album: Hard Candy
Charts: #1 AU, #1 UK, #3 US



Another thing Madonna hadn't done until the new millennium: release a duet as a single. (The closest she'd come was having Babyface on prominent backing vocals in "Take A Bow".) In 2003, she featured on Britney Spears' "Me Against The Music", then launched Hard Candy with this duet with Justin Timberlake (and a bit of help from Timbaland). I like the urgency of "4 Minutes", even if it's not considered an all-time classic.

24. Dress You Up

Year: 1985
Album: Like A Virgin
Charts: #5 AU, #5 UK, #5 US


Madonna was clearly so busy in the '80s that she just didn't have enough time to make music videos for all her singles. And so, like "Causing A Commotion", a live clip was played to promote this fourth and final release from Like A Virgin. Interestingly, it peaked at number 5 across the board in Australia, the UK and the US.

Read more here.

23. I'll Remember

Year: 1994
Album: With Honors soundtrack
Charts: #7 AU, #7 UK, #2 US


Madonna's career is littered with great songs from completely forgettable movies — and here's another: the theme to Joe Pesci comedy With Honors. Did anyone actually ever see that movie? The single served as a palate cleanser between Erotica and Bedtime Stories.

Read more here.

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22. Sorry

Year: 2006
Album: Confessions On A Dance Floor
Charts: #4 AU, #1 UK, #58 US



Australia and the UK were still on board the Madonna disco party train with this second single from Confessions On A Dance Floor, but interest in America dropped right off after "Hung Up". "Sorry" marked the first collaboration between Madonna and Pet Shop Boys (who remixed the song), two decades after the duo considered offering her "Heart".

21. Beautiful Stranger

Year: 1999
Album: Austin Powers: The Spy Who Shagged Me soundtrack
Charts: #5 AU, #2 UK, #19 US


Another soundtrack hit, but unlike With HonorsAt Close RangeThe Next Best Thing and Vision Quest, the film for which "Beautiful Stranger" was recorded was a massive success. The song was another collaboration between Madonna and producer William Orbit, albeit a much poppier one than anything on Ray Of Light or Music.

20. Holiday

Year: 1983
Album: Madonna
Charts: #4 AU, #2 UK, #16 US


It took her three singles, but with this release, Madonna's career was off and running — despite the fact that "Holiday" didn't actually come with an official video, just a variety of TV performances that were aired in different countries.

Read more here.

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19. Lucky Star

Year: 1984
Album: Madonna
Charts: #36 AU, #14 UK, #4 US


With one hit record under her belt, there was no stopping Madonna, with this fourth single from her self-titled debut album kicking off a string of US top 10 hits that would continue until 1989. Locally, "Lucky Star" was unlucky on the ARIA chart.

Read more here.

18. Express Yourself

Year: 1989
Album: Like A Prayer
Charts: #5 AU, #5 UK, #2 US


Accompanied by one of her most expensive videos (directed by David Fincher, and featuring an army of semi-clad men and a scene-stealing cat), "Express Yourself" was radically remixed from the version found on Like A Prayer, and the video mix didn't turn up on one of her albums until 2009's Celebration.

Read more here.

17. Who's That Girl

Year: 1987
Album: Who's That Girl soundtrack
Charts: #7 AU, #1 UK, #1 US


Another song that was absent from an all-Madonna album until Celebration despite being a US and UK number 1, "Who's That Girl" was the theme song from the film of the same name — one of many movies that suggested she should stick to her day job.

Read more here.

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16. Frozen

Year: 1997
Album: Ray Of Light
Charts: #5 AU, #1 UK, #2 US


Madonna could always sense when the time was right for an image overhaul and the transformation into Earth mother was a much-needed shift. The 1996 birth of daughter Lourdes might just have had something to do with the transformation as well. The first single from the career-redefining Ray Of Light, "Frozen" signalled Madonna was still a force to be reckoned with on the charts.

15. Material Girl

Year: 1984
Album: Like A Virgin
Charts: #4 AU, #3 UK, #2 US


The song which gave Madge her most used nickname (and one for which she's expressed distaste) came with a video inspired by Marilyn Monroe film  Gentlemen Prefer Blondes. Coming off the back of the massive success of "Like A Virgin", "Material Girl" confirmed her status as the biggest pop star in the world.

Read more here.

14. Hung Up

Year: 2005
Album: Confessions On A Dance Floor
Charts: #1 AU, #1 UK, #7 US


American Life had been a bit of a disaster, so Madonna went back to doing what had made her a star in the first place: releasing dance floor-friendly club tracks. Featuring a more obvious sample — the synth hook from ABBA's "Gimme Gimme Gimme (A Man After Midnight)" — than Madonna had ever used before, "Hung Up" was a long overdue return to form and chart favour.

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13. Live To Tell

Year: 1986
Album: True Blue
Charts: #7 AU, #2 UK, #1 US


Sure, she'd released a ballad single before, but, teamed with a new stripped back look, "Live To Tell" was the first major image revamp in Madonna's career. The long blonde locks didn't last — they were cropped short for "Papa Don't Preach" — but the public learnt to always expect the unexpected. "Live To Tell" featured in the film At Close Range, which starred her then-husband, Sean Penn.

Read more here.

12. Gambler

Year: 1985
Album: Vision Quest soundtrack
Charts: #10 AU, #4 UK


All but expunged from history, this overlooked single was the second track taken from the Vision Quest soundtrack, a film in which Madonna appeared as a nightclub singer (her first major movie role, even if it wasn't exactly a stretch). "Gambler" is also noteworthy since it features another brilliant middle-eight: "You can't stop me now/Cause I'm right and I'm making advances..."

Read more here.

11. Crazy For You

Year: 1985
Album: Vision Quest soundtrack
Charts: #1 AU, #2 UK, #1 US



Here's the other song from Vision Quest, which was actually released in Australia under the title Crazy For You. Madonna's first ballad, "Crazy For You" was a shock to the system, and critics who'd written her off were forced to reconsider. The song is also remarkable for having peaked at number 2 twice in the UK — in 1985 and again in 1991 when re-released to promote The Immaculate Collection.

Read more here. 

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10. Papa Don't Preach

Year: 1986
Album: True Blue
Charts: #1 AU, #1 UK, #1 US



"Live To Tell" was included on True Blue, but "Papa Don't Preach" kicked off that album's promotion — and came with a clip that featured Madonna's new bleach-blonde hairdo. Also new: more serious lyrical content (about teen pregnancy). And while many of Madonna's singles have remained untouched by other artists, "Papa Don't Preach" was tackled by Kelly Osbourne 16 years later — but the less said about that the better.

Read more here.

9. Vogue

Year: 1990
Album: I'm Breathless
Charts: #1 AU, #1 UK, #1 US



Conceived as a B-side to final Like A Prayer single "Keep It Together", "Vogue" ended up as a single in its own right (and, in Australia, "Keep It Together" wound up as the credited flipside). "Vogue" was also the first single Madonna co-wrote with Shep Pettibone, who had been remixing her tracks for years. The song was shoe-horned into Dick Tracy soundtrack I'm Breathless despite sounding nothing like the rest of the songs.

Read more here.

8. Cherish

Year: 1989
Album: Like A Prayer
Charts: #4 AU, #3 UK, #2 US


Making it three global top 5 hits in a row from Like A Prayer, this playful song written with frequent collaborator Patrick Leonard still puts me in a good mood. The memorable black-and-white clip was directed by photographer Herb Ritts and featured future Madonna boyfriend Tony Ward as one of the mermen.

Read more here.

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7. Jump

Year: 2006
Album: Confessions On A Dance Floor
Charts: #29 AU, #9 UK, #105 US


Possibly a surprising inclusion this high up the list, but this is my favourite Madonna song from the post-'80s era. Thankfully, "Jump" was the fourth single from Confessions..., which meant it received the single edit treatment (something I wish all the tracks from that continually sequenced album were given). 

6. La Isla Bonita

Year: 1987
Album: True Blue
Charts: #6 AU, #1 UK, #4 US



Here's the final single from another album — this time the fifth release from True Blue, which, despite coming out eight months later, still managed to hit top 10s around the world. The first of a number of Madonna tracks to feature Spanish lyrics and sounds, "La Isla Bonita" also came with another new look as her hair went back to a darker hue.

Read more here.

5. Burning Up

Year: 1983
Album: Madonna
Charts: #13 AU



A hit nowhere other than in Australia, Madonna's second single initially sneaked to number 95 on the ARIA chart in late 1983. Once "Holiday" had been a hit, "Burning Up" was reactivated and stormed into the top 20 in early 1984. The song was accompanied by Madonna's first semi-controversial clip in which she writhed around in front of a parked car.

Read more here.

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4. Like A Prayer

Year: 1989
Album: Like A Prayer
Charts: #1 AU, #1 UK, #1 US



Madonna has been scandalous before, but with "Like A Prayer" she really shocked the world, mostly due to the song's provocative video. Controversy and lost Pepsi contracts aside, "Like A Prayer" was her most accomplished single to date and again proved she was more than your average pop singer.

Read more here.

3. Borderline

Year: 1984
Album: Madonna
Charts: #12 AU, #2 UK, #10 US



We're getting close now! The third, fourth or fifth (depending where you lived) single from Madonna, "Borderline" even had a video with a storyline — and wanton property damage.

Read more here.

2. Into The Groove

Year: 1985
Album: Like A Virgin (repackage)
Charts: #1 AU, #1 UK



Madonna was unstoppable in 1985 — and with most fans already owning Like A Virgin, a new track (from film Desperately Seeking Susan) was always going to be huge. But because Madonna had so many songs out, her US record company limited the release of "Into The Groove" (as I mentioned above). In the UK, "Into The Groove" was Madonna's first chart-topper and while it was at number 1, a re-released "Holiday" peaked at number 2.

Read more here.

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1. Open Your Heart

Year: 1986

Album: True Blue

Charts: #16 AU, #4 UK, #1 US

I loved this song from the first time I heard it — and despite competition from over 80 other singles, this fourth release from True Blue is my favourite Madonna track of all time. A relative chart disappointment in Australia, it came with a video that foreshadowed Madonna's underwear-as-outerwear penchant a few years later and cast her in the role of peep show dancer.

Read more here.

Top 20 Non-Singles

Some of Madonna's best songs didn't ever get released as singles. Here are my favourite album tracks and B-sides:

1. "Where's The Party" (from True Blue)
2. "Over And Over" (from Like A Virgin)
3. "Love Makes The World Go Round" (from True Blue)
4. "White Heat" (from True Blue)
5. "Till Death Do Us Part" (from Like A Prayer)
6. "Stay" (from Like A Virgin)
7. "Think Of Me" (from Madonna)
8. "Sky Fits Heaven" (from Ray Of Light)
9. "Physical Attraction" (from Madonna)
10. "Why's It So Hard" (from Erotica)
11. "Amazing" (from Music)
12. "Supernatural" (B-side to "Cherish")
13. "I Know It" (from Madonna)
14. "Words" (from Erotica)
15. "I Deserve It" (from Music)
16. "Time Stood Still" (from The Next Best Thing soundtrack)
17. "Spanish Eyes" (from Like A Prayer)
18. "Don't Stop" (from Bedtime Stories)
19. "Ain't No Big Deal" (B-side to "Papa Don't Preach")
20. "Something To Remember" (from I'm Breathless)

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