Sire Records’ Top 50 Hot 100 Hits: Madonna, Pretenders, Depeche Mode, Talking Heads, Erasure & More

Sire Records, which Seymour Stein co-founded with Richard Gottehrer in 1967 as an independent label before it joined with Warner Bros. in 1976, has generated some of the biggest hits in Billboard Hot 100 history.

As reported April 2, Stein died at age 80. His legendary career began as an intern in Billboard’s New York offices, where, after school, he helped found the Hot 100. “The industry was looking for was a hotter, quicker way of getting chart information,” he recalled to Billboard in 2015. “I was just 16. From the time I was 9 years old, I knew I wanted to be in the music business.”

In honor of Stein’s legacy, Billboard has compiled Sire’s top 50 Hot 100 hits all-time, below.

Madonna is the queen of the recap, with 29 of the 50 songs, including nine of the top 10 and 20 of the top 25.

Of bringing Madonna to Sire, Stein said, “I signed her because I believed in Mark Kamins, who I thought was the greatest DJ, and he wanted to be a producer. So, I gave him some money to bring me an artist, and the third or fourth thing he brought me was Madonna. I was very involved in the beginning. Then I realized, ‘This woman is smarter than all of us. Just get out of her way.’”

“Seymour Stein Has Left Us! I need to catch my breath. He Was one of the most influential Men in my Life!! He changed and Shaped my world,” Madonna wrote in an Instagram post April 3, featuring a screenshot from her 1992 “Deeper and Deeper” video, in which Stein made a cameo.

“Not only did Seymour hear me but he Saw me and my Potential! For this I will be eternally grateful!,” she shared. “I am weeping as I write this down. Words cannot describe how I felt at this moment after years of grinding and being broke and getting every door slammed in my face. Anyone who knew Seymour knew about his passion for music and his impeccable taste. He had an Ear like no other!”

Among other acts on the retrospective below: Pretenders, Depeche Mode, Talking Heads, Erasure, Seal and the late Tommy Page, the latter of whom also worked at Billboard, as publisher in the early 2010s, and presented Stein with the first Billboard Industry Icon Award in 2012. (Wrote Stein in tribute in 2017, “One thing nearly everyone who knew him said about Tommy was that he made them feel special, that they were the only person in the room, and that’s just one reason why so many people adored him.”)

“We are so sorry to hear about the passing of legendary US music guru Seymour Stein, who was such a huge part of Erasure’s US success,” Erasure posted on its social media accounts April 3.

“Talking Heads are deeply saddened to learn that Seymour Stein has died,” the band wrote on Instagram April 3. “He was our champion. He fought bravely for us and he remained loyal to us until the end. Some people can spot a diamond in the rough and Seymour was one of them. He offered us a record deal after seeing us only one time at CBGB, before even we felt we were ready. He waited impatiently for eighteen months until we finally said yes to his offer.

“To hear him sing one of our own songs to us while barreling down Broadway in a Checker cab was one of our life’s great delights. We say this with respect to his beautiful daughter Mandy and to all of the Sire Records family. He was a mensch that we and the music business will never forget.”

Sire Records’ Top 50 Hot 100 Hits:

Rank, Title, Artist, Label Listing / Peak Pos., Date:

1, “Like a Virgin,” Madonna, Sire/Warner Bros. / No. 1 (six weeks), 12/22/1984
2, “Vogue,” Madonna, Sire/Warner Bros. / No. 1 (three weeks), 5/19/1990
3, “Take a Bow,” Madonna, Maverick/Sire/Warner Bros. / No. 1 (seven weeks), 2/25/1995
4, “Kiss From a Rose,” Seal, ZTT/Sire/Warner Bros. / No. 1 (one week), 8/26/1995
5, “Justify My Love,” Madonna, Sire/Warner Bros. / No. 1 (two weeks), 1/5/1991
6, “Like a Prayer,” Madonna, Sire/Warner Bros. / No. 1 (three weeks), 4/22/1989
7, “Papa Don’t Preach,” Madonna, Sire/Warner Bros. / No. 1 (two weeks), 8/16/1986
8, “Live To Tell,” Madonna, Sire/Warner Bros. / No. 1 (one week), 6/7/1986
9, “Pop Muzik,” M, Sire/Warner Bros. / No. 1 (one week), 11/3/1979
10, “Open Your Heart,” Madonna, Sire/Warner Bros. / No. 1 (one week), 2/7/1987

11, “Who’s That Girl,” Madonna, Sire/Warner Bros. / No. 1 (one week), 8/22/1987
12, “Material Girl,” Madonna, Sire/Warner Bros. / No. 2, 3/23/1985
13, “I’ll Be Your Everything,” Tommy Page, Sire/Warner Bros. / No. 1 (one week), 4/14/1990
14, “I’ll Remember,” Madonna, Maverick/Sire/Warner Bros. / No. 2, 5/28/1994
15, “Causing a Commotion,” Madonna, Sire/Warner Bros. / No. 2, 10/24/1987
16, “Express Yourself,” Madonna, Sire/Warner Bros. / No. 2, 7/15/1989
17, “True Blue,” Madonna, Sire/Warner Bros. / No. 3, 11/15/1986
18, “Cherish,” Madonna, Sire/Warner Bros. / No. 2, 10/7/1989
19, “La Isla Bonita,” Madonna, Sire/Warner Bros. / No. 4, 5/2/1987
20, “Secret,” Madonna, Maverick/Sire/Warner Bros. / No. 3, 11/5/1994

21, “Couldn’t Get It Right,” Climax Blues Band, Sire/ABC / No. 3, 5/21/1977
22, “Back on the Chain Gang,” Pretenders, Sire/Warner Bros. / No. 5, 3/19/1983
23, “Angel,” Madonna, Sire/Warner Bros. / No. 5, 6/29/1985
24, “This Used To Be My Playground,” Madonna, Sire/Warner Bros. / No. 1 (one week), 8/8/1992
25, “Dress You Up,” Madonna, Sire/Warner Bros. / No. 5, 10/5/1985
26, “Lucky Star,” Madonna, Sire/Warner Bros. / No. 4, 10/20/1984
27, “Enjoy the Silence,” Depeche Mode, Sire/Reprise / No. 8, 7/14/1990
28, “Tainted Love,” Soft Cell, Sire/Warner Bros. / No. 8, 7/17/1982
29, “Crazy,” Seal, Sire/Warner Bros. / No. 7, 9/7/1991
30, “Hocus Pocus,” Focus, Sire/Famous / No. 9, 6/2/1973

31, “Don’t Get Me Wrong,” Pretenders, Sire/Warner Bros. / No. 10, 12/27/1986
32, “Borderline,” Madonna, Sire/Warner Bros. / No. 10, 6/16/1984
33, “Keep It Together,” Madonna, Sire/Warner Bros. / No. 8, 3/31/1990
34, “Deeper and Deeper,” Madonna, Maverick/Sire/Warner Bros. / No. 7, 1/30/1993
35, “Burning Down the House,” Talking Heads, Sire/Warner Bros. / No. 9, 10/22/1983
36, “People Are People,” Depeche Mode, Sire/Warner Bros. / No. 13, 8/3/1985
37, “Erotica,” Madonna, Maverick/Sire/Warner Bros. / No. 3, 10/24/1992
38, “Chains of Love,” Erasure, Sire/Reprise / No. 12, 10/29/1988
39, “Brass in Pocket (I’m Special),” Pretenders, Sire/Warner Bros. / No. 14, 5/31/1980
40, “I’ll Stand by You,” Pretenders, Sire/Warner Bros. / No. 16, 12/3/1994

41, “A Little Respect,” Erasure, Sire/Reprise / No. 14, 3/4/1989
42, “Policy of Truth,” Depeche Mode, Sire/Reprise / No. 15, 10/20/1990
43, “Rescue Me,” Madonna, Sire/Warner Bros. / No. 9, 3/23/1991
44, “Hanky Panky,” Madonna, Sire/Warner Bros. / No. 10, 7/28/1990
45, “Holiday,” Madonna, Sire/Warner Bros. / No. 16, 1/28/1984
46, “Get Over Yourself,” Eden’s Crush, 143/London-Sire / No. 8, 3/31/2001
47, “Wild Wild Life,” Talking Heads, Sire/Warner Bros. / No. 25, 12/6/1986
48, “Oh Father,” Madonna, Sire/Warner Bros. / No. 20, 1/6/1990
49, “Middle of the Road,” Pretenders, Sire/London-Sire / No. 19, 2/11/1984
50, “Far Behind,” Candlebox, Maverick/Sire/Warner Bros. / No. 18, 10/1/1994

Sire Records’ Top 50 Hot 100 Hits recap is based on actual performance on the weekly Billboard Hot 100 chart. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. To ensure equitable representation of the biggest hits from each era, certain time frames were weighted to account for the difference between turnover rates from those years.