The 30 Best Shaggy Songs Of All Time, Ranked

The career of Dancehall megastar Shaggy has been, in a word – enviable.

With multiple Grammy Award wins and nods, the recent recipient of the Jamaica Reggae Industry Association’s (JaRIA) Icon Award continues blazing a path forward for Reggae and Dancehall. Shaggy, a legendary voice that began its journey to prominence in the early 90s, would eventually rule the roost with an impressive stint of hits, asserting himself as one of the most commercially successful artists to ever come out of Jamaica.

In this article, we’ve narrowed down 30 of his best songs from his extensive catalog. Just want a list? Check out our handy Spotify playlist at the end.

30. Leave It To Me (ft. Brian and Tony Gold)

In Leave It To Me, featuring Brian and Tony Gold, Shaggy gives fans a more soulful, laid-back vocal delivery – a stark contrast from his heavy and rugged way of toasting. The smooth delivery by the Grammy winner perfectly sets the romantic stage for the sweet sounds of Brian and Tony Gold to take over on the hook, melodically singing – almost a whisper – “Leave it to me, baby we can turn on the heat, baby.”

Released: 2000
Album: Hot Shot
Producer: Robert Livingston

29. Ready Fi Di Ride

In keeping with the theme of the album Clothes Drop, Ready Fi Di Ride is intended to be a lyrical and rhythmic, heavy-hitting Dancehall party-starter. The easy-to-love beat drops, then ‘Mr. Lover Lover’ confidently takes a not-so-subtle route to the point: “Put up your hand if yuh ready fi di ride, you want a man weh point your heels to the sky.”

Released: 2005
Album: Clothes Drop
Producer: Tony ‘CD’ Kelly

28. Wild 2nite  (ft. Olvia)

The lead single on Shaggy’s sixth album Clothes Drop, Wild 2nite features R&B Pop singer Olivia. The record peaked at No. 61 on the UK Singles Chart, and has been a major club banger in European and urban spaces.

Released: 2005
Album: Clothes Drop
Producer: Shaun ‘Sting International’ Pizzonia, Armando Colon

27. Why Me Lord?

Released in 2000, Why Me Lord? finds Shaggy addressing the age-old issue of cheating, which forms the blueprint for other hits the star would go on to produce, like It Wasn’t Me. This time, Shaggy not only gets caught in the act, but owns up to it in a chorus that is just as widely recognized as Shaggy himself.

Released: 2000
Album: Hot Shot
Producer: Robert Livingston

26. Keep’n It Real

Keep’n It Real features a reggae-infused melody, underpinned by a smooth, rhythmic bassline as Shaggy addresses themes of authenticity and staying true to oneself in a world filled with pretense and superficiality.

Released: 2000
Album: Hot Shot
Producer: Gordon Dukes, Shaggy, Shaun ‘Sting International’ Pizzonia

25. That Love

As a former marine himself, Shaggy’s That Love was dedicated to the US military. “Sacrifices are made on both sides, military personnel and dependents. I personally have felt that being deployed in the first Gulf War and being away from my loved ones. We give thanks for their service. Semper Fi,” he explained. The song also received a remix from producer Tony ‘CD’ Kelly, with added vocals from Dancehall artist Alkaline.

Released: 2016
Album: n/a
Producer: Scott Storch, Diego Ave

24. Hope

Hope was first recorded for the soundtrack of the film For Love of the Game, and later appeared on the Hot Shot album. Unlike some of his more upbeat, danceable tunes, Hope delves into deeper, more introspective territory, touching on themes of aspiration, personal growth, and perseverance.

Released: 1999
Album: Hot Shot
Producer: Shaun ‘Sting International’ Pizzonia

23. Dance and Shout (ft. Pee Wee)

This list wouldn’t be complete without including Hot Shot’s Dance and Shout, featuring Pee Wee. The track is a reworking of Shake Your Body Down To The Ground, a 1979 hit by The Jacksons. Shaggy once again teamed up with Terry Lewis and Jimmy Jam for the dance-floor favorite. The club-ready banger peaked at No. 4 in the Billboard Bubbling Under Hot 100 and No. 19 on the UK Singles chart in 2001.

Released: 2000
Album: Hot Shot
Producer: Jimmy Jam and Terry Lewis

22. Piece Of My Heart (ft. Marsha)

Released on his 1997 album Midnight Lover, Shaggy explores the perils of relationships in Piece Of My Heart, featuring vocalist Marsha. It was a fun and modern take on the Piece of My Heart number originally recorded by Erma Franklin in 1976, and written by Jerry Ragovoy and Bert Berns. Shaggy’s version peaked at No. 72 on the Billboard Hot 100, and No. 7 on the UK Singles chart.

Released: 1997
Album: Midnight Lover
Producer: Shaggy

21. Don’t Make Me Wait (with Sting)

It’s the Grammy-winning collaboration Rock and Reggae never knew they needed. In 2018, Shaggy teamed up with the legendary English superstar Sting for the album 44/876, and among its impressive track list, ‘Don’t Make Me Wait’ stood out exceptionally well. The mellow-sounding, vibrant track combines the best of Shaggy and Sting vocally, and sheds light on why the two seem to have such natural chemistry on 44/876. 

Released: 2018
Album: 44/876
Producer: Shaun ‘Sting International’ Pizzonia

20. Soon Be Done

As a precursor to his later hits, Soon Be Done is a must-listen for fans of Shaggy’s work, offering a fascinating glimpse into  the early stages of Shaggy’s career and his development as an artist.   The song’s catchy melody and memorable chorus contribute to its overall appeal, making it a standout track from his debut album.

Released: 1993
Album: Pure Pleasure
Producer: Shaggy

19. What’s Love (ft. Akon)

Shaggy teamed up with Senegalese-American singer Akon for What’s Love, a reggae fusion track about the struggles and complexities of romantic relationships.   

Released: 2007
Album: Intoxication
Producer: Abou ‘Bu’ Thiam

18. Bridges (ft. Chronixx)

Shaggy and Chronixx’s dynamic pairing in Bridges brought the song’s powerful message of unity and connection to life.   

Released: 2013
Album: Out Of Many, One Music
Producer: Sly & Robbie, Shaun ‘Sting International’ Pizzonia

17. Why You Treat Me So Bad (ft. Grand Puba)

Another note-worthy release from his Boombastic era, ‘Why You Treat Me So Bad’ is a funky Hip Hop-inspired take about a man begging for the attention of the one who he admires most. It was released as the second single from that album, his third, and notably draws inspiration from Bob Marley’s ‘Mr. Brown’. The song peaked at No. 8 on the US Bubbling Under Hot 100, and No. 11 on the UK Singles chart.

Released: 1995
Album: Boombastic
Producer: Robert Livingston, Shaun ‘Sting International’ Pizzonia

16. Big Up (ft. Rayvon)

The rub-a-dub Dancehall track Big Up, which features Rayvon, was the fourth and final single from Shaggy’s debut album, Pure Pleasure.

Released: 1993
Album: Pure Pleasure
Producer: Shaun ‘Sting International’ Pizzonia

15. Freaky Girl (ft. The Kraft)

Shaggy’s Hot Shot album was replete with hits, and Freaky Girl, featuring The Kraft, was another of them. An upbeat Hip-Hop rhythm drives the fun-loving song that celebrates girls who love to have a good time, and it makes sufficient room for Shaggy’s clever use of euphemisms throughout. The track shuns perfection and conservatism and embraces naughtiness. It peaked at No. 22 on the Billboard Bubbling Under Hot 100.

Released: 2000
Album: Hot Shot
Producer: Shaun ‘Sting International’ Pizzonia

14. You Girl (ft. Ne-Yo)

Shaggy and Ne-Yo’s You Girl is a contemporary R&B and pop track, with a classic Reggae foundation.   The harmonious and captivating tune is a shining example of Shaggy’s ability to innovate and collaborate with diverse talents, while still honoring Reggae’s roots. 

Released: 2013
Album: Out Of Many, One Music
Producer: Sly & Robbie, Shaun ‘Sting International’ Pizzonia

13. Luv Me Luv Me (ft. Janet Jackson, and ft. Samantha Cole)

The hit single Luv Me, Luv Me, featuring Janet Jackson, came to fruition after Michael Jackson’s producer, Terry Lewis, reached out to Shaggy to do a song for the soundtrack of the movie, How Stella Got Her Groove Back in 1998. Later, when Shaggy wanted to add the track to his album Hot Shot, Virgin Records withheld the rights to Janet Jackson’s vocals, whom the Dancehall star described working with as “a complete nightmare.” In the year 2000, the song was re-recorded, with Samantha Cole taking the place of Jackson for his album. The original, with Jackson’s vocals, peaked at No. 76 on the Billboard Hot 100 in 1998.

Released: 1998, 2000
Album: How Stella Got Her Groove Back Soundtrack, Hot Shot
Producer: Jimmy Jam, Terry Lewis

12. Church Heathen

With guest vocals from Ninja Man, Shaggy’s Church Heathen stirred controversy when it called out religious hypocrisy. Though not released in the US, the song was a major hit in the Caribbean, and is featured in the soundtrack of the 2008 video game, Grand Theft Auto IV.

Released: 2007
Album: Intoxication
Producer: Tony ‘CD’ Kelly, Shaun ‘Sting International’ Pizzonia

11. Bonafide Girl (ft. Rik Rok and Tony Gold)

An earworm of a bop, Bonafide Girl, which features Rik Rok and Tony Gold, was released in 2007 and samples the 1967 rocksteady hit “007 Shanty Town” by ska stars Desmond Dekkar and the Aces.

Released: 2007
Album: Intoxication
Producer: Shaun ‘Sting International’ Pizzonia

10. Fight This Feeling (ft. Beres Hammond)

In 2013, Shaggy teamed up with legendary Lover’s Rock crooner, Beres Hammond, to record the soulful track, Fight This Feeling, for the Out Of Many One Music album. The official music video includes behind-the-scenes clips showing the making of the heartfelt and moving collaboration about the ups and downs of relationships.

Released: 2013
Album: Out Of Many, One Music
Producer: Sly & Robbie, Shaun ‘Sting International’ Pizzonia

9. In The Summertime (ft. Rayvon)

Though a cover of British rock band Mungo Jerry’s 1970 hit written by the lead singer, Ray Dorset, In The Summertime is uniquely transformed by Shaggy and Rayvon, making it another of Shaggy’s memorable collaborations. The song celebrates the carefree days of having fun in the summer with beautiful women and friends. It peaked at No. 3 on the US Billboard Hot 100 and No. 5 on the UK Singles chart. In The Summertime is certified Silver in the UK, for sales exceeding 200,000 units.

Released: 1995
Album: Boombastic
Producer: Shaggy, Rayvon

8. I Need Your Love (ft. Mohombi, Faydee, Costi)

I Need Your Love, featuring Congolese-Swedish singer Mohombi, Lebanese-Australian singer Faydee, and Romanian singer Costi, is one of Shaggy’s more recent hits, centering on the theme of love and longing. The fusion track peaked at No. 66 on the Billboard Hot 100, and was later certified Gold in the United States for surpassing 500,000 units in sales. It peaked at No. 36 on the UK Singles chart, before it was certified Silver in the country for sales exceeding 200,000 copies.

Released: 2014
Album: n/a
Producer: Constantin ‘Costi’ Ionita

7. Strength Of A Woman

Shaggy’s Strength of A Woman celebrates women’s unique qualities and unwavering strength, making it a timeless anthem for female empowerment. Just last year, Barbados Labour Party leader and current Prime Minister of Barbados, Mia Motley, used the hit song in her re-election campaign. “When I analyze my whole life and what has happened, women have played a very important part. I’m from a single-parent family. My mom is like my mom and dad. She’s my world. So (this album is) just me paying homage to ladies all around,” Shaggy said in a 2002 interview with CNN.

Released: 2002
Album: Lucky Day
Producer: Shaun ‘Sting International’ Pizzonia

6. Mad Mad World (ft. Sizzla, Collie Buddz)

Shaggy joined forces with Reggae icon Sizzla Kalonji and Bermudan singer Collie Buddz for Mad Mad World, a melodic and standout track from his album Intoxication.

Released: 2007
Album: Intoxication
Producer:

5. Hey Sexy Lady (ft. Brian and Tony Gold)

Shaggy’s Hey Sexy Lady celebrates the beauty and allure of a woman, originally with the help of the duo Brian and Tony Gold. There are several versions of the song, including cuts with Sean Paul and Will Smith. The music video, featuring a sultry model dancing alongside Shaggy, helped the track to gain widespread attention. It peaked at No. 97 on the US Billboard Hot R&B and Hip-Hop Songs chart, and No. 10 on the UK Singles chart.

Released: 2002
Album: Lucky Day , Sexy Lady Explosion Riddim
Producer: Christopher Birch

4. Oh Carolina

Shaggy’s breakthrough hit, Oh Carolina is a ska-inspired, contemporary track which mirrors the 1958 megahit ska song of the same name, originally sung by the Folkes Brothers, with production from Prince Buster. Shaggy’s version gained heavy recognition overseas after the track was used in the film Sliver. It became the first of Shaggy’s songs to hit No. 1 on the UK Singles chart. In the US, it peaked at No. 59 on the Billboard Hot 100.

Released: 1993
Album: Pure Pleasure
Producer: Shaun ‘Sting International’ Pizzonia

3. Boombastic

With the smooth and sultry rendition of Boombastic, in which Shaggy describes himself as “Mr. Lover Lover,” he reaffirms his versatility as an artist. The album Boombastic, which won the Grammy award for Best Reggae Album in 1996, achieved Platinum certification in the US on November 4 that year, selling one million units. The single, which went to No. 3 on the Billboard Hot 100, achieved its Platinum status on August 29, 1995. In the United Kingdom, Boombastic peaked at No. 1 in November 1995 and was later certified Platinum in the country for selling 600,000 units.

Released: 1995
Album: Boombastic
Producer: Robert Livingston, Shaun ‘Sting International’ Pizzonia

2. Angel (ft. Rayvon)

Angel‘s catchy melody, heartfelt lyrics, and seamless blending of Reggae, R&B, and Pop elements resulted in another chart-topper from Shaggy’s multi-platinum album, Hot Shot. The track cleverly samples two well-known hits: Angel of the Morning by Merrilee Rush and The Joker by Steve Miller Band. It reached No. 1 in over 12 countries, including the US, and the UK, where it is certified Gold.

Released: 2000
Album: Hot Shot
Producer: Shaun ‘Sting International’ Pizzonia

1. It Wasn’t Me (ft. Rik Rok)

In It Wasn’t Me, Shaggy offers a foolproof escape plan after his friend, Rik Rok, was caught ‘red-handed’ in the act of cheating. “Say it wasn’t you,” he advises, setting the tone for his biggest international hit. The catchy breakthrough song topped the charts in several countries, including the US Billboard Hot 100 and the UK Singles chart. The song was nominated at the 44th Annual Grammy Awards for Best Pop Collaboration with Vocals, and it’s currently certified quadruple Platinum in the UK.

Released: 2000
Album: Hot Shot
Producer: Shaun ‘Sting International’ Pizzonia

Here’s a Spotify playlist of the best Shaggy songs: