25 Most Popular Songs For The Millennial Generation

Posted by , Updated on May 20, 2024

We all have our favorite’s songs but considering the diversity of songs that were most popular during the years when the Generation Y came around (which was from 1982/1983 until 2004) rating songs for this particular generation is difficult. Therefore this list is based only on the US Billboard Hot 100 Charts. We combined all the Top 1 hits with the songs that remained the most number of weeks in the chart. These 25 most popular songs for the millennial generation exhibited a collaboration of genres, a wide range of powerful vocal dynamics and an infusion of digitally enhanced music.

Centerfold – The J. Geils Band

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Although it was released a year before the first set of millenials were born, this single shot up to the top of the charts on February 1982 and stayed there for 6 weeks.


Like a Virgin – Madonna

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Also topping the charts for 6 weeks by the end of 1984, it was said that this song and “Material Girl” which is from the same album made Madonna an icon. Like a Virgin is one of the most memorable songs Madonna has made in her entire career.


Say, Say, Say – Paul McCartney and Michael Jackson

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This pleading kind of love song was the seventh top ten hit for Michael Jackson which stayed on the top spot for 6 weeks but it was produced for Paul McCartney’s fifth solo album, Pipes of Peace. Although it had mixed reviews, it went on to hit number one in more than 20 other countries.


Flashdance… What a Feeling – Irene Cara

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With several covers by different artists around the globe, this soundtrack from the 1983 film Flashdance went on to win an Academy Award and a Golden Globe Award for Best Original Song.


Eye of the Tiger – Survivor

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Released on May 1982 as the theme song for Sylvester Stallone’s Rocky III, it ranked 5th in the 1980-1989 End of Decade U.S. Billboard Hot 100. Survivor gained a double platinum award for this chart topper.


Billie Jean – Michael Jackson

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Although it was almost scrapped off from the album because of the co-producer, Michael Jackson recorded it anyway and garnered many awards including two Grammies, one American Music Award and an induction into the Music Video Producers Hall of Fame.


Ebony and Ivory – Paul McCartney and Stevie Wonder

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The fourth biggest hit of 1982 was a duet inspired simply by the black and white keys of the piano and more figuratively about integration and racial harmony. It was the longest running chart topper for Paul McCartney’s solo career second only to “Hey Jude”.


Every Breath You Take – The Police

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The 1984 Grammy Awards’ Song of the Year and 8-week chart topper was The Police’s signature song which in 2010 was estimated to have generated between a quarter to a third of Sting’s music publishing income. Although people tend to see this song in a positive light, Sting insists it’s a song of obsession, jealousy and surveillance for a lost lover. So if you’re planning to add this to your wedding playlist, think again.


Foolish – Ashanti

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For a debut song to stay at the top of the charts for 10 straight weeks is an amazing feat for any artist. Especially if it won awards such as a Grammy and Soul Train Award. Ashanti’s phenomenal song gained recognition as the third best selling physical single of 21st Century as of June, 2012.


Dilemma – Nelly featuring Kelly Rowland

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Released in two separate albums by Nelly, an American rap artist, and Kelly Rowland’s, one of Destiny’s Child founding members; Dilemma is one of three songs that stayed at the top of the charts for 10 weeks straight.


Maria Maria – Santana featuring The Product G&B

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Maria, Maria not only was a 10 week chart topper but was the namesake of five restaurants across the United States which where opened by the legendary guitarist himself, Carlos Santana, in collaboration with Chef Roberto Santibañez. The hip swaying Latin inspired song which was released in 1999 was the second successful musical collaboration by the musician.


Independent Women – Destiny’s Child

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The song first appeared as part of the soundtrack to the 2000 film Charlie’s Angels and was later included in Destiny’s Child’s third studio album, Survivor. Its one of four songs in this list to stay at the top of the charts for 11 straight weeks. Several club remixes were also released by the girl group.


I’ll Be Missing You – Puff Daddy & Faith Evans ft. 112

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One of two songs on this list written in memory of a loved one; it was released the same year Christopher “The Notorious B.I.G.” Wallace was murdered. Puff Daddy, Faith Evans and 112′s Grammy Award-winning hit soared to the top of the charts and stayed there for 11 weeks making it the longest running No. 1 hip-hop song in history until another song on this list broke it’s record.


I Swear – All-4-One

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It’s the only cover rendition on this list and probably the best decision All-For-One made in their career. With a very slight difference from the original, the soulful blending of vocals gave a more flavorful harmony and an up-and-coming spirit to the original country version by John Michael Montgomery.


Un-Break My Heart – Toni Braxton

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Toni Braxton was said to have disliked this sultry but sorrowful song. However L.A. Reid convinced her to record it, a decision that brought tantamount fame to Toni. Her powerful and expressive belting clinched the #1 spot on the charts for 11 weeks straight earning Toni a Grammy Award for Best Female Pop Vocal Performance.


Yeah! – Usher featuring Lil Jon & Ludacris

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This critically acclaimed Crunk & B hit, an incorporation of crunk and R & B, was a team effort between Usher featuring Lil Jon, Ludacris. Topping the charts for 11 weeks, a Grammy Award for Best Rap/Song Collaboration and ranking second on the decade end Billboard Hot 100 highlighted the musical ingenuity present in this song.


Lose Yourself – Eminem

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Eminem’s hardcore hip-hop track was the first ever rap song to win an Academy Award for Best Original Song in 2002. It also received the Grammy Awards for Best Male Rap Solo Performance and Best Rap Song and was one of three rap songs, the highest of the three at that, which made it to Rolling Stone’s 500 Greatest Songs of All Time released in 2004. It was also the first single from the soundtrack of 8 mile, Eminem’s critically acclaimed box office film in 2002.


Smooth – Santana ft. Rob Thomas

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Winning three Grammy Awards, Record of the Year, Song of the Year, and Best Pop Collaboration with Vocals, this Latin rock fusion between Carlos Santana, Rob Thomas of Matchbox Twenty and song writer Itaal Shur, portrayed hot summer nights and sultry romance with a lot more hip swaying and electrifying guitar strains making it a chart topper for 12 weeks. Smooth was rewritten from an original track penned by Shur which was titled Room 17. Thomas followed through with the new lyrics and melody and got his inspiration from his wife, Marisol Maldonado.


The Boy Is Mine – Brandy & Monica

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Inspired by The Jerry Springer Show and the 1982 hit “The Girl is Mine”, this contemporary R&B song by Brandy and Monica was about two women fighting over a man. The collaboration was also to dispel rumors that they had a rivalry between them. 14 years later, in 2012, the long time friends sang their 1998 13 week chart topper as well as their new duet “It All Belongs To Me”.


End of the Road – Boyz II Men

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Originally the soundtrack of Eddie Murphy’s film, Boomerang, this Motown label topped the charts for 13 weeks making it the most successful single of the record company beating Diana Ross and Lionel Richie’s “Endless Love”. In 1992, it also beat Elvis Presley’s 11 week chart topper “Hound Dog”, a song which held that record for 36 years.


Macarena (Bayside Boys Mix) – Los Del Rio

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Staying in the Hot 100 chart for 6 weeks and nailing the top spot for 14 weeks is a massive feat for a remix version of any song in the millenial generation. The Bayside remix of this upbeat iconic Spanish song originally released by Los del Rio, and remixed by the Bayside Boys shot the one hit wonder to worldwide fame and made it a staple at parties, clubs and almost all festive events around the globe. Thanks to a local flamenco teacher, the Spanish duo’s inspiration, this monstrous hit united the world with the same beat and equally famous dance routine.


Candle in the Wind ’97 – Elton John

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The second tribute on this list is Elton John’s rewrite and re-recorded version of the 1973 single of the same title in memory of Diana, Princess of Wales who died in a car crash in Paris, France. The only time he sang the revised version was at her funeral in Westminster Abbey on the 6th of September, 1997. Although he sings the original version in his concerts, he has repeatedly refused to sing the version written for his dear friend. The international hit stayed on top for 14 weeks.


I’ll Make Love to You – Boyz II Men

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Ranked 17th on Billboard Chart’s All Time Top 10, Boyz to Men’s second sensational hit won the 1995 Grammy Award for Best R&B Performance by a Duo or Group with Vocals and two American Music Awards for Favorite Pop/Rock Single and Favorite Soul/R&B Single. This is the second 14 weeks chart topper of the group which will be beaten later on by one of their amazingly successful collaborations.


I Will Always Love You – Whitney Houston

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Dolly Parton’s original country version of this internationally acclaimed hit was already a chart topper 18 years before Whitney Houston recorded her own version for the movie, The Bodyguard. This powerfully moving rendition will forever be remembered as the song which gave Houston the best selling single by a female artist in music history.


One Sweet Day – Mariah Carey & Boyz II Men

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Written for sufferers of AIDS which were growing in number at that time and to all those who have lost their loved ones, One Sweet Day is the longest running number one song in the US chart history staying atop for 16 weeks. It also topped the charts in several countries around the world and was ranked by Rolling Stone’s Best Collaboration of All Time. The simple video filmed in 1996 was lauded by the critics as a wise choice and it’s simplicity paid homage to the selfless and universal message of the song.