[2025] Smooth sailing at karaoke and work! Safe, fail-proof songs that won’t miss when singing karaoke with your boss or at business entertainment
Unlike karaoke with friends of a similar age or close coworkers, when it comes to karaoke as a second round after client dinners or drinks with bosses who are one or two generations older, you can’t help but be careful with your song choices.
Many new professionals are probably wondering what songs they should sing.
In this article, we introduce foolproof karaoke picks: timeless classics loved across generations—centered on the hit songs from your bosses’ youth—as well as recent buzzworthy tracks widely known even in mainstream households.
We’ve also selected Showa–Heisei era songs familiar to younger people via TikTok and more, so you’re sure to find something you can sing!
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[2025] Smooth sailing at karaoke and work! Safe, crowd-pleasing songs that won't miss for karaoke with your boss or clients (41–50)
KanadeSukima Switch
Since its release in 2004, Sukima Switch’s “Kanade” has been highly popular and frequently performed on television.
It has also been featured in films and commercials, and its recognition is very high thanks to numerous cover versions by various artists.
As a slightly bittersweet ballad about parting and new departures, it’s best suited for a calm, mellow time slot if you plan to sing it at karaoke.
[2025] Smooth sailing at karaoke and work! Safe, inoffensive songs you can’t go wrong with for karaoke with your boss or clients (51–60)
LOVE MachineMorning Musume
The seventh single by Morning Musume, an idol group that debuted under the production of Tsunku♂ from Sharam Q.
With a sound reminiscent of late-1960s disco updated for the modern era, impactful lyrics and choreography, and a catchy melody, this track rapidly boosted the group’s popularity and name recognition.
Widely known across generations, it’s a classic karaoke staple—singing and dancing to it with a manager in their 30s who was of the target generation when it was released is sure to get the crowd going.
Be kind to othersTHE BLUE HEARTS
This song by THE BLUE HEARTS has continued to be loved by many people for its simple, powerful lyrics and catchy melody.
It was released as a single in 1987 and came out on CD the following year.
It was also used as an insert song in the 1989 film “Juliet Game,” which helped it reach an even wider audience.
Hiroto Kōmoto’s deep, rich vocals leave a strong impression, and the feelings embedded in each lyric resonate with listeners.
It’s a song that can win cross-generational empathy if you sing it at karaoke with your boss or clients.
MPRINCESS PRINCESS
Released in 1989, PRINCESS PRINCESS’s smash-hit ballad “M” was the B-side to “DIAMONDS,” the first single in history to sell over a million copies.
With lyrics by drummer Kyoko Tomita and music by vocalist Kaori Okui, the song beautifully captures a woman’s heart.
Its straightforward words resonate with women, and many listeners have been moved to tears by the melody’s aching tenderness and quiet strength.
It’s become a classic go-to ballad for karaoke.
StoryAI
It’s a moving ballad that virtually every Japanese person has heard.
Released by AI in May 2005, the song carries a warm message: “Treasure today, this very moment.” It captured many hearts, reaching No.
8 on the Oricon charts.
In 2014, it was also chosen as the Japanese ending theme for the film Big Hero 6, and it continues to be loved across generations.
This is a safe choice to sing at karaoke after a dinner with your boss or clients—its easy-to-sing melody and relatable lyrics are sure to create a pleasant atmosphere.
Sayonara, baby.Miliyah Kato
This is a medium-tempo R&B-style song that expresses a bittersweet longing for love.
The lyrics, which portray feelings for a lover who is drifting away, are sure to resonate with many people.
Released as a single in September 2008, it is Miliyah Kato’s 13th single.
A newly arranged version was later released in November 2019.
It’s also well-suited for singing at business entertaining occasions with superiors or clients, and it has a universal appeal that spans generations.
With its simple melody and lyrics, it’s easy to sing at karaoke, making it a recommended choice for business-related karaoke gatherings.
Goodbye ElegyMasaki Suda
In addition to his outstanding work as an actor, Masaki Suda is also active as a singer.
Although he balances it with his acting career, his authentic vocals and performances captivate many listeners.
This song is one of his signature tracks, and for many people, it may have been their first introduction to his music.
Since it consistently ranks high in karaoke charts, it’s a safe choice even for work-related karaoke gatherings with a wide range of age groups!