71. Jellybean, “Sidewalk Talk”
Hot 100 Peak: Number 18
Madonna penned the first single to be credited to her then-boyfriend, New York DJ John “Jellybean” Benitez, and handled vocal duties on its chorus. (The breathy Catharine Buchanan, who passed away in 2001, sang the verses.) Similar in style to the ramped-up club music that made tracks like the Benitez-produced “Holiday” early-Eighties radio staples, “Sidewalk Talk” distills the essence of New York — full of fast-moving possibility and flash, but to be handled with caution in order to be survived. M.J.
67. Madonna, “Like a Virgin”
Hot 100 Peak: Number One
If the hits from Madonna’s 1983 debut established her as a star, it was the title track from 1984’s Like a Virgin that vaulted her into icon status, rocketing to the top of the Hot 100 in its sixth week on the chart. Madonna has played up the ambiguity of the lyric, which has been interpreted in many ways (most famously and explicitly in Quentin Tarantino’s Reservoir Dogs), but the song was originally conceived by songwriter Billy Steinberg as a tender ballad inspired by a new love after a depressing heartbreak. It was Madonna herself, however, who suggested the title of the parody “Weird Al” Yankovic later recorded, “Like a Surgeon.” A.S.
2. Madonna, “Borderline”
Hot 100 Peak: Number 10
“I dared to believe this was going to be huge beyond belief, the biggest thing I’d ever had, after I heard ‘Borderline,'” Seymour Stein, the record man who signed Madonna, recalled. “The passion that she put into that song, I thought, there’s no stopping this girl.” His gut was right on target: The fifth and final single from Madonna’s 1983 debut album was her first to hit the Top 10. The melodic synth-a-palooza with the plunky low end was one of two on the LP penned by Reggie Lucas, who used a drum machine instead of a live drummer for the first time on the tune, doubling a synth bass with Anthony Jackson on electric bass guitar (“They’re playing so tight you can’t tell the difference,” Lucas said). Madonna turned in a sweetly-sung, restrained but emotional vocal (her voice wavers just so when she gets to “Feels like I’m going to lose my mind”) about a beau who has her heart twisted. The radio remix, which trims nearly three minutes from the tune, boasts one of Madge’s most iconic fade-outs, standing by as she “la la la”s into the void. C.G.