Debut of the Monthly Music Challenge

This challenge below was recently posted on the Charm City Trivia social media pages (Fb link). I’ll be posting music challenges like these once a month. Below is the challenge, followed by the answers along with some comments and links. I had fun doing it—hope you find it interesting as well.

Bob’s Monthly Music Challenge
Same title, different song!


There are at least two songs with each of these titles that were hits. For each title, name the artist who reached the highest peak on the Billboard Hot 100. If there are multiple songs that hit #1, list the one that spent the most weeks at the top. For a bigger challenge, also list the runner-up for each song title!

If you choose to look up the answers, that’s okay, but please refrain from posting them.

1. “Angel”
2. “Crazy”
3. “Don’t Be Cruel”
4. “Fame”
5. “Hello”
6. “Just The Way You Are”
7. “Love Song”
8. “Photograph”
9. “Show Me Love”
10. “Without Me”

Hint: The Billboard Hot 100 debuted in August 1958, so any song released before that never peaked on that chart!


Here’s a bit more on songs with those titles:

1. “Angel”
Highest peaking: Shaggy with Rayvon (#1 in 2001)
Runner up: Aerosmith (#3 in 1988)
Others: Sarah McLachlan (#4 in 1999); Madonna (#5 in 1985)
This one was close! Shaggy seemed to come out of nowhere in 2001 when “It Wasn’t Me” went to #1. It was his first hit in over four years, and he rode that, as the follow-up song, “Angel” also hit the top. It was his last top 40 hit. Aerosmith’s “Angel” was also part of a comeback. The Permanent Vacation album followed their collaboration with Run-DMC on a cover of “Walk This Way” and was their first successful album in over a decade.

2. “Crazy”
Highest peaking: Gnarls Barkley (#2 in 2006)
Runner up: Seal (#7 in 1991)
Others: Patsy Cline (#9 in 1961); K-Ci and JoJo (#11 in 2001); Icehouse (#14 in 1988); Aerosmith (#17 in 1994)
Note: Britney Spears recorded “(You Drive Me) Crazy,” which reached #10 in 1999.
Gnarls Barkley’s biggest hit takes the win. Cee Lo Green had been around for a while, but that song was what made him very famous. Seal’s “Crazy” was his debut single. Willie Nelson wrote Patsy Cline’s “Crazy,” which was her only top 10 song that reached the Hot 100.  It went to #2 on the country chart.

3. “Don’t Be Cruel”
Highest peaking: Cheap Trick (#4 in 1988)
Runner up: Bobby Brown (#8 in 1988)
Others: Bill Black’s Combo (#11 in 1961)
Trick question of sorts! As stated in the question, the Hot 100 debuted in August 1958, so the iconic Elvis Presley song (1956) never hit that chart. It was covered by Bill Black’s Combo and by Cheap Trick, who released it as a follow-up to their #1 hit, “The Flame.” Bobby Brown’s “Don’t Be Cruel” was the title track from his classic New Jack Swing album. In a chart oddity, for two weeks in October 1988, both Cheap Trick and Bobby Brown’s songs named “Don’t Be Cruel” were in the top 10 at the same time!

4. “Fame”
Highest peaking: David Bowie (#1 in 1975)
Runner up: Irene Cara (#4 in 1980)
Others: no other significant hits with that name
Although it feels like some of his other songs are more well-known or have help up better, “Fame” and “Let’s Dance” were David Bowie’s only #1 hits. The late Irene Cara had a career before starring in the movie musical, Fame, but for many, this movie and soundtrack marked her star turn. She would later hit #1 with another movie song, from the 1983 movie, Flashdance.

5. “Hello”
Highest peaking: Adele (#1 for 10 weeks, 2015-16)
Runner up: Lionel Richie (#1 for 2 weeks in 1984)
Others: no other Top 40 hits with that name
Here are two heavy-hitters, both of which hit #1. Adele’s first single from 25 spent 10 weeks on top in 2015-2016. Lionel Richie’s ballad, “Hello,” reached the top for two weeks in May 1984, and went on to become the subject of more than a few memes. Surprisingly, no other song titled “Hello” came close to that level of success, but three songs with “Hello” in the title reached #1. Those are “Hello, Dolly!” by Louis Armstrong, “Hello, Goodbye” by the Beatles and “Hello, I Love You” by the Doors, each of which has a comma after the word, “Hello.”

6. “Just the Way You Are”
Highest peaking: Bruno Mars (#1 in 2010)
Runner up: Billy Joel (#3 in 1978)
Others: no other Top 40 hits with that name
Just the Way You Are” was the first solo hit for Bruno Mars; it went all the way to the top in October 2010 and earned him a Grammy for Best Male Pop Vocal Performance. Billy Joel’s “Just the Way You Are” was the lead single from The Stranger and was his first top 10 hit. It also won two major Grammys for the singer/songwriter, Song of the Year and Record of the Year.

7. “Love Song”
Highest peaking: The Cure (#2 in 1989)
Runner up: Sara Bareilles (#4 in 2008)
Others: Tesla (#10 in 1990); Anne Murray (#12 in 1984)
The Cure’s “Love Song” was also known as “Lovesong” but the two-word spelling was what was on the Billboard chart. “Love Song” was the debut hit for Sara Bareilles, and though it seems hard to believe, is her only top 10 hit to date. Although it peaked at #4, it spent 19 weeks in the top 10. “Love Song” is also the title of the only recorded duet by Madonna and Prince, an unreleased album cut from Like a Prayer.


8. “Photograph”
Highest peaking: Ringo Starr (#1 in 1973)
Runner up: Nickelback (#2 in 2005)
Others: Ed Sheeran (#10 in 2015); Def Leppard (#12 in 1983); J. Cole (#14 in 2018)
Ringo Starr and George Harrison co-wrote “Photograph,” which became Ringo’s first #1 hit in November 1973. Harrison played 12-string guitar on the track. The sometimes-maligned band, Nickelback hit #2 for a week in October 2005 with “Photograph.” They did better with it on the Adult Top 40 chart—18 weeks at #1!!

9. “Show Me Love”
Highest peaking: Robin S (#5 in 1993)
Runner up: Robyn (#7 in 1997)
Others: no other Top 40 hits with that name
Here we have two dance music singers with similar names, both hits in the ‘90s. The Robin S song “Show Me Love” is a house music classic that heavily inspired and was sampled in Beyoncé’s “Break My Soul,” which just won a Grammy for Best Dance/Electronic Recording. Swedish singer Robyn was a teenager when her first two U.S. hits, “Do You Know (What It Takes)” and “Show Me Love,” both peaked at #7 in 1997.

10. “Without Me”
Highest peaking: Halsey (#1 in 2019)
Runner up: Eminem (#2 in 2002)
Others: no other Top 40 hits with that name
Halsey’s “Without Me” was #1 for two weeks in January 2019 and was the #1 song on pop radio of that year. She had hit #1 as a featured artist in 2016 on “Closer” by the Chainsmokers, and “Without Me” was her first #1 on her own. Eminem came close to hitting #1 in 2002 with his “Without Me,” but got stuck in the #2 spot for five weeks behind Nelly’s megahit, “Hot in Herre.”

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