On this day, Nov. 3, in hip-hop history...

1990: "Ice Ice Baby," the breakout single from Miami rapper Vanilla Ice, became the first hip-hop track to reach No. 1 on the Billboard Hot 100.

The Queen-sampling song was released in July of 1990 on Ice's debut album To The Extreme. As a single, "Ice Ice Baby" was the B-side track to one of Ice's other songs titled "Play That Funky Music." When DJ David Morales saw that fans were responding more to the B-side track, he began to promote "Ice Ice Baby" over "Play That Funky Music" and the idea caught on. Though not many people took Ice seriously as a rapper at the time, "Ice Ice Baby" was infectious enough to garner major radio love across the country. "Ice Ice Baby" stayed at the No. 1 spot in the U.S. from Nov. 3, 1990 to Nov. 10, 1990. Around that time, the song also topped the charts in Australia, Belgium, the Netherlands, New Zealand, Ireland and the United Kingdom. This was a huge step for making hip-hop an acceptable genre to mainstream media.

To date, "Ice Ice Baby" remains Vanilla Ice's most recognizable and successful song. The single, as well as his album, To The Extreme, is certified platinum in sales.

The Longest-Running Hot 100 No. 1 Rap Songs Ever

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Furious 7 Los Angeles Premiere Sponsored by Dodge

Wiz Khalifa is still on top. The Pittsburgh MC's latest hit, "See You Again" featuring Charlie Puth, is closing in on the title of the longest-running hip-hop song to top the Billboard Hot 100 chart, having spent 11 of the past 12 weeks as the biggest song in the country (Taylor Swift and Kendrick Lamar's "Bad Blood" was the only cut to interrupt the reign for a single week). With no signs of slowing down, that got us at XXL thinking: What are the longest-running hip-hop songs to land atop the Hot 100?

In order to find out, we dug through the charts over the past 30-plus years to get to the bottom of it, ranking every song either by a rapper or with a featured rap verse that has ever climbed to No. 1. But before we get to the songs, here are a few fun facts we uncovered during our research.

Ed. Note (July 8): "See You Again" remained at No. 1 for a 12th week in today's charts, putting it in a tie for the longest-running No. 1 hip-hop song on the Hot 100 ever. This article has been updated to reflect that.

—First "Rap" Song to Hit No. 1: Blondie's "Rapture," largely credited with helping legitimize the early hip-hop pioneers like the Sugar Hill Gang and Grandmaster Flash
—Most Weeks at No. 1: T.I. (28 weeks), Eminem (25 weeks), Diddy (24 weeks), 50 Cent (23 weeks), Nelly (23 weeks), Flo Rida (18 weeks), Ludacris (18 weeks)
—Rappers With the Most No. 1 Songs: Eminem (5), Ludacris (5), T.I. (4), 50 Cent (4), Nelly (4)
Drake, Kendrick Lamar, Slim Thug, Juelz Santana, Petey Pablo, MC Shan, Caddillac Tah, Ma$e, Timbaland, Static Major, Mystikal, Dr. Dre, LL Cool J, Nate Dogg, Murphy Lee, Juicy J, Jeezy, Soulja Slim, Paul Wall, Kool Moe Dee and Yung Joc have all landed at No. 1 as a featured artist, but never as the main artist
Soulja Boy, Mims, Iggy Azalea, Sir Mix-a-lot, Lil Kim, Coolio, Terror Squad, Cali Swag District, Lauryn Hill, Juvenile, Chamillionaire, B.o.B, Twista, D4L and Vanilla Ice have all had one song hit the top spot and never made it back to the top of the chart
2pac, Lil Wayne, Jay Z, Kanye West, Snoop Dogg and Lauryn Hill are just a few iconic rappers who have only had one of their songs hit the top spot
XXL Freshman With No. 1 Songs (As Main Artist): Wiz Khalifa (2), B.o.B, Macklemore (2) and Iggy Azalea
—Soundtrack Songs: 8 MileBad Boys IIFurious 7 and Moulin Rouge
Rihanna, Katy Perry, Taylor Swift, Beyoncé, Mariah Carey and Jennifer Lopez helped rappers land atop the chart 12 times

Now check out every hip-hop song that has charted at No. 1 on the Hot 100, in order from longest-running to the tracks that touched the peak for a single week, still an impressive stat to have on the resume. Pressure's on, Wiz. —Dan Rys

1-lose-yourself

"Lose Yourself"

Artist: Eminem
Album: 8 Mile Soundtrack
Weeks at No. 1: 12
Dates at No. 1: November 9, 2002 - February 1, 2003

2-usher-yeah

"Yeah!"

Artist: Usher featuring Lil Jon and Ludacris
Album: Confessions
Weeks at No. 1: 12
Dates at No. 1: February 28, 2004 - May 22, 2004

3-robin-thicke-blurred-lines

"Blurred Lines"

Artist: Robin Thicke featuring Pharrell and T.I.
Album: Blurred Lines
Weeks at No. 1: 12
Dates at No. 1: June 22, 2013 - September 14, 2013

5-wiz-khalifa-see-you-again

"See You Again"

Artist: Wiz Khalifa featuring Charlie Puth
Album: Furious 7 Soundtrack
Weeks at No. 1: 12
Dates at No. 1: April 25, 2015 - June 6, 2015; June 13, 2015 - present

4-puff-missing-you

"I'll Be Missing You"

Artist: Puff Daddy and Faith Evans featuring 112
Album: No Way Out
Weeks at No. 1: 11
Dates at No. 1: June 14, 1997 - August 30, 1997

6-nelly-dilemma

"Dilemma"

Artist: Nelly featuring Kelly Rowland
Album: Nellyville
Weeks at No. 1: 10
Dates at No. 1: August 17, 2002 - October 5, 2002; October 19, 2002 - November 9, 2002

7-kanye-gold-digger

"Gold Digger"

Artist: Kanye West featuring Jamie Foxx
Album: Late Registration
Weeks at No. 1: 10
Dates at No. 1: September 17, 2005 - November 26, 2005

8-flo-rida-low

"Low"

Artist: Flo Rida featuring T-Pain
Album: Mail On Sunday
Weeks at No. 1: 10
Dates at No. 1: January 5, 2008 - March 15, 2008

9-50-cent-in-da-club

"In Da Club"

Artist: 50 Cent
Album: Get Rich Or Die Tryin'
Weeks at No. 1: 9
Dates at No. 1: March 8, 2003 - May 10, 2003

10-outkast-hey-ya

"Hey Ya!"

Artist: OutKast
Album: Speakerboxxx/The Love Below
Weeks at No. 1: 9
Dates at No. 1: December 13, 2003 - February 14, 2004

11-50-cent-candy-shop

"Candy Shop"

Artist: 50 Cent featuring Olivia
Album: The Massacre
Weeks at No. 1: 9
Dates at No. 1: March 5, 2005 - May 7, 2005

12-kriss-kross-jump

"Jump"

Artist: Kriss Kross
Album: Totally Krossed Out
Weeks at No. 1: 8
Dates at No. 1: April 25, 1992 - June 20, 1992

13-bone-thugs-crossroads

"Tha Crossroads"

Artist: Bone Thugs-N-Harmony
Album: E. 1999 Eternal
Weeks at No. 1: 8
Dates at No. 1: May 18, 1996 - July 13, 1996

14-Beyonce-Crazy-In-Love

"Crazy In Love"

Artist: Beyoncé featuring Jay Z
Album: Dangerously In Love
Weeks at No. 1: 8
Dates at No. 1: July 12, 2003 - September 6, 2003

15-snow-informer

"Informer"

Artist: Snow featuring MC Shan
Album: 12 Inches of Snow
Weeks at No. 1: 7
Dates at No. 1: March 13, 1993 - May 1, 1993

16-waterfalls

"Waterfalls"

Artist: TLC
Album: CrazySexyCool
Weeks at No. 1: 7
Dates at No. 1: July 8, 1995 - August 26, 1995

17-nelly-hot-herre

"Hot In Herre"

Artist: Nelly
Album: Nellyville
Weeks at No. 1: 7
Dates at No. 1: June 29, 2002 - August 17, 2002

18-ciara-goodies

"Goodies"

Artist: Ciara featuring Petey Pablo
Album: Goodies
Weeks at No. 1: 7
Dates at No. 1: September 11, 2004 - October 30, 2004

19-Rihanna-Umbrella

"Umbrella"

Artist: Rihanna featuring Jay Z
Album: Good Girl Gone Bad
Weeks at No. 1: 7
Dates at No. 1: June 9, 2007 - July 28, 2007

20-soulja-boy-crank-that

"Crank That (Soulja Boy)"

Artist: Soulja Boy
Album: Souljaboytellem.com
Weeks at No. 1: 7
Dates at No. 1: September 15, 2007 - September 29, 2007; October 6, 2007 - November 10, 2007

21-ti-whatever-you-like

"Whatever You Like"

Artist: T.I.
Album: Paper Trail
Weeks at No. 1: 7
Dates at No. 1: September 6, 2008 - September 27, 2008; October 4, 2008 - October 18, 2008; November 1, 2008 - November 15, 2008

22-love-the-way-you-lie-rihanna

"Love The Way You Lie"

Artist: Eminem featuring Rihanna
Album: Recovery
Weeks at No. 1: 7
Dates at No. 1: July 31, 2010 - September 18, 2010

23-iggy-fancy

"Fancy"

Artist: Iggy Azalea featuring Charli XCX
Album: The New Classic
Weeks at No. 1: 7
Dates at No. 1: June 7, 2014 - July 26, 2014

24-diddy-cant-nobody-hold-me-down

"Can't Nobody Hold Me Down"

Artist: Puff Daddy featuring Ma$e
Album: No Way Out
Weeks at No. 1: 6
Dates at No. 1: March 22, 1997 - May 3, 1997

25-jlo-aint-it-funny

"Ain't It Funny (Murder Remix)"

Artist: Jennifer Lopez featuring Ja Rule and Caddillac Tah
Album: J to tha L-O! The Remixes
Weeks at No. 1: 6
Dates at No. 1: March 9, 2002 - April 20, 2002

26-nelly-furtado-promiscuous

"Promiscuous"

Artist: Nelly Furtado featuring Timbaland
Album: Loose
Weeks at No. 1: 6
Dates at No. 1: July 8, 2006 - August 19, 2006

27-tip-live-your-life

"Live Your Life"

Artist: T.I. featuring Rihanna
Album: Paper Trail
Weeks at No. 1: 6
Dates at No. 1: October 18, 2008 - October 25, 2008; November 15, 2008 - December 13, 2008; December 20, 2008 - December 27, 2008

28-flo-rida-right-round

"Right Round"

Artist: Flo Rida featuring Ke$ha
Album: R.O.O.T.S.
Weeks at No. 1: 6
Dates at No. 1: February 28, 2009 - April 11, 2009

29-Katy-Perry-California-Gurls-Featuring-Snoop-Dogg-katy-perry-34970264-1920-1080

"California Gurls"

Artist: Katy Perry featuring Snoop Dogg
Album: Teenage Dream
Weeks at No. 1: 6
Dates at No. 1: June 19, 2010 - July 31, 2010

30-MACKLEMORE-THRIFT-SHOP

"Thrift Shop"

Artist: Macklemore and Ryan Lewis featuring Wanz
Album: The Heist
Weeks at No. 1: 6
Dates at No. 1: February 2, 2013 - March 2, 2013; April 6, 2013 - April 20, 2013

31-sir-mix-lot-baby-got-back

"Baby Got Back"

Artist: Sir Mix-A-Lot
Album: Mack Daddy
Weeks at No. 1: 5
Dates at No. 1: July 4, 1992 - August 8, 1992

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2001 MTV Movie Awards show

"Lady Marmalade"

Artist: Christina Aguilera, Lil Kim, Mya and Pink
Album: Moulin Rouge Soundtrack
Weeks at No. 1: 5
Dates at No. 1: June 2, 2001 - July 7, 2001

33-jlo-im-real

"I'm Real (Murder Remix)"

Artist: Jennifer Lopez featuring Ja Rule
Album: J.Lo
Weeks at No. 1: 5
Dates at No. 1: September 8, 2001 - September 29, 2001; October 20, 2001 - November 3, 2001

34-chris-brown-run-it

"Run It!"

Artist: Chris Brown featuring Juelz Santana
Album: Chris Brown
Weeks at No. 1: 5
Dates at No. 1: November 26, 2005 - December 31, 2005

35-beyonce-check-on-it-featuring-bun-slim-thug

"Check On It"

Artist: Beyoncé featuring Slim Thug
Album: #1's
Weeks at No. 1: 5
Dates at No. 1: February 4, 2006 - March 11, 2006

36-lil-wayne-lollipop

"Lollipop"

Artist: Lil Wayne featuring Static Major
Album: Tha Carter III
Weeks at No. 1: 5
Dates at No. 1: May 3, 2008 - May 10, 2008; May 31, 2008 - June 28, 2008

37-empire-state-of-mind-jay-feat-alicia-keys

"Empire State Of Mind"

Artist: Jay Z featuring Alicia Keys
Album: The Blueprint 3
Weeks at No. 1: 5
Dates at No. 1: November 28, 2009 - January 2, 2009

38-katy-perry-et

"E.T."

Artist: Katy Perry featuring Kanye West
Album: Teenage Dream
Weeks at No. 1: 5
Dates at No. 1: April 9, 2011 - April 30, 2011; May 7, 2011 - May 21, 2011

39-Macklemore-Ryan-lewis-cantholdus6

"Can't Hold Us"

Artist: Macklemore and Ryan Lewis featuring Ray Dalton
Album: The Heist
Weeks at No. 1: 5
Dates at No. 1: May 18, 2013 - June 22, 2013

40-Joe-Stutter

"Stutter"

Artist: Joe featuring Mystikal
Album: My Name Is Joe
Weeks at No. 1: 4
Dates at No. 1: Februrary 24, 2001 - March 24, 2001

41-TLC-Creep-Single-Cover-Art

"Creep"

Artist: TLC
Album: CrazySexyCool
Weeks at No. 1: 4
Dates at No. 1: January 28, 1995 - February 25, 1995

42-blackstreet-no-diggity

"No Diggity"

Artist: Blackstreet featuring Dr. Dre and Queen Pen
Album: Another Level
Weeks at No. 1: 4
Dates at No. 1: November 9, 1996 - December 7, 1996

43-jlo-ll-cool-j

"All I Have"

Artist: Jennifer Lopez featuring LL Cool J
Album: This Is Me... Then
Weeks at No. 1: 4
Dates at No. 1: February 8, 2003 - March 8, 2003

44-50-cent-21-questions

"21 Questions"

Artist: 50 Cent featuring Nate Dogg
Album: Get Rich Or Die Tryin'
Weeks at No. 1: 4
Dates at No. 1: May 31, 2003 - June 28, 2003

45-shake-ya-tailfeather

"Shake Ya Tailfeather"

Artist: Nelly featuring P. Diddy and Murphy Lee
Album: Bad Boys II Soundtrack
Weeks at No. 1: 4
Dates at No. 1: September 6, 2003 - October 4, 2003

46-Eminem-The-Monster

"The Monster"

Artist: Eminem featuring Rihanna
Album: The Marshall Mathers LP 2
Weeks at No. 1: 4
Dates at No. 1: December 21, 2013 - January 18, 2014

47-katy-perry-dark-horse

"Dark Horse"

Artist: Katy Perry featuring Juicy J
Album: Prism
Weeks at No. 1: 4
Dates at No. 1: February 8, 2014 - March 8, 2014

48-coolio-gangstas-paradise

"Gangsta's Paradise"

Artist: Coolio featuring L.V.
Album: Gangsta's Paradise
Weeks at No. 1: 3
Dates at No. 1: September 9, 1995 - September 30, 1995

49-biggie-hypnotize

"Hypnotize"

Artist: The Notorious B.I.G.
Album: Life After Death
Weeks at No. 1: 3
Dates at No. 1: May 3, 1997 - May 24, 1997

50-will-smith-jiggy

"Gettin' Jiggy Wit It"

Artist: Will Smith
Album: Big Willie Style
Weeks at No. 1: 3
Dates at No. 1: March 14, 1998 - April 4, 1998

51-lean-back

"Lean Back"

Artist: Terror Squad (Fat Joe and Remy Ma)
Album: True Story
Weeks at No. 1: 3
Dates at No. 1: August 21, 2004 - September 11, 2004

52-snoop-dogg-drop-it-hot

"Drop It Like It's Hot"

Artist: Snoop Dogg featuring Pharrell
Album: R&G (Rhythm and Gangsta): The Masterpiece
Weeks at No. 1: 3
Dates at No. 1: December 11, 2004 - January 1, 2005

53-justin-timberlake-my-love

"My Love"

Artist: Justin Timberlake featuring T.I.
Album: FutureSex/LoveSounds
Weeks at No. 1: 3
Dates at No. 1: November 11, 2006 - December 2, 2006

54-chris-brown-kiss-kiss

"Kiss Kiss"

Artist: Chris Brown featuring T-Pain
Album: Exclusive
Weeks at No. 1: 3
Dates at No. 1: November 10, 2007 - December 1, 2007

55-usher-love-club-jeezy

"Love In This Club"

Artist: Usher featuring Jeezy
Album: Here I Stand
Weeks at No. 1: 3
Dates at No. 1: March 15, 2008 - April 5, 2008

56-like-a-g6

"Like A G6"

Artist: Far East Movement featuring The Cataracs and Dev
Album: Free Wired
Weeks at No. 1: 3
Dates at No. 1: October 30, 2010 - November 13, 2010; November 27, 2010 - December 4, 2010

57-blondie-rapture

"Rapture"

Artist: Blondie
Album: Autoamerican
Weeks at No. 1: 2
Dates at No. 1: March 28, 1981 - April 11, 1981

58-tupac-all-eyez-on-me

"How Do U Want It"/"California Love"

Artist: 2pac featuring K-Ci & JoJo/2pac featuring Dr. Dre and Roger Troutman
Album: All Eyez On Me
Weeks at No. 1: 2
Dates at No. 1: July 13, 1996 - July 27, 1996

59-the-notorious-big-mo-money-mo-problems

"Mo Money Mo Problems"

Artist: The Notorious B.I.G. featuring Puff Daddy and Ma$e
Album: Life After Death
Weeks at No. 1: 2
Dates at No. 1: August 30, 1997 - September 13, 1997

60-lauryn-hill-doo-wop

"Doo Wop (That Thing)"

Artist: Lauryn Hill
Album: The Miseducation of Lauryn Hill
Weeks at No. 1: 2
Dates at No. 1: November 14, 1998 - November 28, 1998

61-mariah-carey-heartbreaker

"Heartbreaker"

Artist: Mariah Carey featuring Jay Z
Album: Rainbow
Weeks at No. 1: 2
Dates at No. 1: October 9, 1999 - October 23, 1999

62-ja-rule-always-on-time

"Always On Time"

Artist: Ja Rule featuring Ashanti
Album: Pain Is Love
Weeks at No. 1: 2
Dates at No. 1: February 23, 2002 - March 9, 2002

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63-juvenile-slow-motion-getty

"Slow Motion"

Artist: Juvenile featuring Soulja Slim
Album: Juve The Great
Weeks at No. 1: 2
Dates at No. 1: August 7, 2004 - August 21, 2004

64-nelly-Sweatsuit-cover

"Grillz"

Artist: Nelly featuring Paul Wall, Ali and Gipp
Album: Sweatsuit
Weeks at No. 1: 2
Dates at No. 1: January 21, 2006 - February 4, 2006

65-chamillionaire-ridin

"Ridin'"

Artist: Chamillionaire featuring Krayzie Bone
Album: The Sound Of Revenge
Weeks at No. 1: 2
Dates at No. 1: June 3, 2006 - June 17, 2006

66-Ludacris-Release-Therapy

"Money Maker"

Artist: Ludacris featuring Pharrell
Album: Release Therapy
Weeks at No. 1: 2
Dates at No. 1: October 28, 2006 - November 11, 2006

67-akon-wanna-love-you-ft-snoop-dogg

"I Wanna Love You"

Artist: Akon featuring Snoop Dogg
Album: Konvicted
Weeks at No. 1: 2
Dates at No. 1: December 2, 2006 - December 16, 2006

68-mims-this-is-why-hot

"This Is Why I'm Hot"

Artist: Mims
Album: Music Is My Savior
Weeks at No. 1: 2
Dates at No. 1: March 10, 2007 - March 24, 2007

69-fergie-glamorous

"Glamorous"

Artist: Fergie featuring Ludacris
Album: The Dutchess
Weeks at No. 1: 2
Dates at No. 1: March 24, 2007 - April 7, 2007

70-jay-sean-wayne-down

"Down"

Artist: Jay Sean featuring Lil Wayne
Album: All Or Nothing
Weeks at No. 1: 2
Dates at No. 1: October 17, 2009 - October 24, 2009; October 31, 2009 - November 7, 2009

71-bob-nothin-on-you

"Nothin' On You"

Artist: B.o.B featuring Bruno Mars
Album: B.o.B Presents: The Adventures of Bobby Ray
Weeks at No. 1: 2
Dates at No. 1: May 1, 2010 - May 15, 2010

72-flo-rida-whistle

"Whistle"

Artist: Flo Rida
Album: Wild Ones
Weeks at No. 1: 2
Dates at No. 1: August 25, 2012 - September 1, 2012; September 15, 2012 - September 22, 2012

SBK Records

73-vanilla-ice-baby

"Ice Ice Baby"

Artist: Vanilla Ice
Album: To The Extreme
Weeks at No. 1: 1
Dates at No. 1: November 3, 1990 - November 10, 1990

74-wild-wild-west

"Wild Wild West"

Artist: Will Smith featuring Dru Hill and Kool Moe Dee
Album: Willennium
Weeks at No. 1: 1
Dates at No. 1: July 24, 1999 - July 31, 1999

75-outkast-ms-jackson

"Ms. Jackson"

Artist: OutKast
Album: Stankonia
Weeks at No. 1: 1
Dates at No. 1: February 17, 2001 - February 24, 2001

76-b2k-bump-bump-bump

"Bump Bump Bump"

Artist: B2K featuring P. Diddy
Album: Pandemonium!
Weeks at No. 1: 1
Dates at No. 1: February 1, 2003 - February 8, 2003

77-ludacris-stand-up

"Stand Up"

Artist: Ludacris featuring Shawnna
Album: Chicken-N-Beer
Weeks at No. 1: 1
Dates at No. 1: December 6, 2003 - December 13, 2003

78-outkast-way-you-move

"The Way You Move"

Artist: OutKast featuring Sleepy Brown
Album: Speakerboxxx/The Love Below
Weeks at No. 1: 1
Dates at No. 1: February 14, 2004 - February 21, 2004

79-twista-slow-jamz

"Slow Jamz"

Artist: Twista featuring Kanye West and Jamie Foxx
Album: Kamikaze (and, later, The College Dropout)
Weeks at No. 1: 1
Dates at No. 1: February 21, 2004 - February 28, 2004

80-d4l-laffy-taffy

"Laffy Taffy"

Artist: D4L
Album: Down For Life
Weeks at No. 1: 1
Dates at No. 1: January 14, 2006 - January 21, 2006

81-t-pain-buy-drank-shawty

"Buy U A Drank (Shawty Snappin')"

Artist: T-Pain featuring Yung Joc
Album: Epiphany
Weeks at No. 1: 1
Dates at No. 1: May 26, 2007 - June 2, 2007

82-eminem-crack-a-bottle

"Crack A Bottle"

Artist: Eminem featuring 50 Cent and Dr. Dre
Album: Relapse
Weeks at No. 1: 1
Dates at No. 1: February 21, 2009 - February 28, 2009

83-taio-cruz-break-your-heart-featuring-ludacris

"Break Your Heart"

Artist: Taio Cruz featuring Ludacris
Album: Rokstarr
Weeks at No. 1: 1
Dates at No. 1: March 20, 2010 - March 27, 2010

84-eminem-not-afraid

"Not Afraid"

Artist: Eminem
Album: Recovery
Weeks at No. 1: 1
Dates at No. 1: May 22, 2010 - May 29, 2010

85-rihanna-drake-looking

"What's My Name?"

Artist: Rihanna featuring Drake
Album: Loud
Weeks at No. 1: 1
Dates at No. 1: November 20, 2010 - November 27, 2010

86-wiz-black-yellow

"Black And Yellow"

Artist: Wiz Khalifa
Album: Rolling Papers
Weeks at No. 1: 1
Dates at No. 1: February 19, 2011 - February 26, 2011

87-taylor-swift-kendrick

"Bad Blood"

Artist: Taylor Swift featuring Kendrick Lamar
Album: 1989
Weeks at No. 1: 1
Dates at No. 1: June 6, 2015 - June 13, 2015