Top 25 #1 Hits - 1990 - 1999

These songs were chosen for spending the most weeks at #1 on Billboard's Hot 100. In case of ties, most weeks in the Top 10 were used, followed by the most weeks in the Top 40 and Hot 100.

Title	Artist	Peak Year	Weeks
			@ #1	Top 10	Top 40	Top 100
One Sweet Day	Mariah Carey & Boyz II Men	95	16	19	26	27
Macarena	Los Del Rio	96	14	23	37	40
I'll Make Love To You	Boyz II Men	94	14	22	31	33
Candle In The Wind/ Something About The Way You Look Tonight	Elton John	97	14	17	28	42
I Will Always Love You	Whitney Houston	92	14	16	24	26
End Of The Road	Boyz II Men	92	13	19	28	32
The Boy Is Mine	Brandy & Monica	98	13	18	27	27
Smooth	Santana w/ Rob Thomas	99	12	30	50	58
Un-Break My Heart	Toni Braxton	96	11	25	37	42
I Swear	All-4-One	94	11	18	26	30
I'll Be Missing You	Puff Daddy & Faith Evans w/ 112	97	11	17	29	33
Fantasy	Mariah Carey	95	8	16	23	25
Dreamlover	Mariah Carey	93	8	14	26	29
That's The Way Love Goes	Janet Jackson	93	8	14	20	23
Jump	Kris Kros	92	8	13	18	21
Tha Crossroads	Bone Thugs-N-Harmony	96	8	12	16	20
Waterfalls	TLC	95	7	18	28	34
Take A Bow	Madonna	95	7	15	27	30
Can't Help Falling In Love	UB40	93	7	15	23	29
This Is How We Do It	Montell Jordan	95	7	14	24	29
Informer	Snow	93	7	13	19	25
(Everything I Do) I Do It For You	Bryan Adams	91	7	10	17	22
Black Or White	Michael Jackson	91	7	10	15	20
The Sign	Ace of Base	96	6	21	33	41
Because You Loved Me	Celine Dion	95	6	19	30	33

Two things to note. First, there was a change in the way Billboard tracked data on November 30, 1991. The use of Broadcast Data Systems and SoundScan resulted in longer runs in the Hot 100. As such, there are probably deserving songs from 1990 and 1991 that got left off due to the change.

Second, until December 5, 1998, the Hot 100 only included songs that were commercially available as singles. With the popularity of CDs, fewer and fewer singles were released. Eventually, Billboard realized they had to make a change and began to track album cuts as well. The following songs had the longest runs at #1 on the Hot 100 Airplay chart:

Title	Artist	Weeks at #1
Iris	Goo Goo Dolls	18
Don't Speak	No Doubt	16
Torn	Natalie Imbruglia	11
Fly	Sugar Ray	6

Source: Whitburn, Joel. The Billboard Book of Top 40 Hits. 9th ed. New York: Billboard, 2010. 868, 869. Print.