[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 at work! Safe, reliable songs that won’t miss the mark for karaoke with your boss or clients (51–60)
First LoveHikaru Utada
This is one of Hikaru Utada’s signature songs, capturing the bittersweetness of first love and a deep, abiding affection.
The lyrics—remarkably mature for something written at age 16—and the delicate emotional expression resonated with many listeners.
Released in March 1999, it peaked at No.
2 on the Oricon singles chart and became a massive hit, holding the No.
1 spot on karaoke charts for 15 consecutive weeks.
The track is included on the album First Love and remains a timeless classic in Japanese music history, still cherished today.
It’s a song that bridges generations, making it a safe choice to sing at karaoke even during work-related gatherings with bosses or clients.
It offers the courage to move past heartbreak and step into a new love.
Yes, with pleasure.Kent on this side
For Kocchi no Kento, a “multi-creator” with truly multifaceted talents, 2024 was a breakthrough year.
His track Hai Yorokonde, which was also performed at the 75th NHK Kouhaku Uta Gassen that same year, was released in May 2024 and became an explosive viral hit.
As of 2025, it has racked up an astonishing 170 million views on YouTube.
Kocchi no Kento is known for his strong vocal skills honed through a cappella, but Hai Yorokonde sits in a relatively low key and doesn’t require a wide vocal range.
While the lyrics are a bit fast, it sounds great if you keep to the rhythm.
It’s also extremely well-known, so definitely give it a try at karaoke.
crescent moonAyaka
Mikazuki is a love song by Ayaka released in 2006! It’s a ballad about a long-distance relationship and was used as a TV show theme and in a mobile phone commercial.
The chorus goes quite high and uses falsetto, so it might require a bit of vocal skill.
If you’re singing it at karaoke, it’s best for a slightly calmer moment rather than the peak of the excitement.
The One and Only Flower in the WorldSMAP
SMAP, the national idol group that sadly disbanded in 2016.
Their signature song would have to be “Sekai ni Hitotsu Dake no Hana” (“The Only Flower in the World”).
Released in 2003, it achieved triple million sales.
It was originally included on the album “SMAP 015/Drink! SMAP,” which came out on July 4, 2002.
The members reportedly liked this track the most on the album.
It will continue to be passed down across generations.
[2025] Smooth in Karaoke and at Work! Safe, Non-Miss Songs for Company Bosses and Client Entertainment (61–70)
paprikaFoorin
Released ahead of other Olympic support songs as NHK’s 2020 cheer song, this track was produced by the hugely popular Kenshi Yonezu, and the kids’ unit Foorin also created a big buzz.
It feels like there’s hardly anyone who hasn’t heard this song by now—it’s known across generations.
If you’re singing it at karaoke with colleagues or business associates, being able to do even just the chorus dance will likely hype things up even more!
A Perfect SkyBONNIE PINK
Known for her crystal-clear vocals and profound lyrics, BONNIE PINK’s signature hit features a pop melody that evokes the cheerful spirit of summer.
Released in June 2006, the song gained huge attention as the commercial theme for Shiseido’s ANESSA sunscreen.
There’s even an anecdote that the chorus alone captured so many hearts it led to the creation of a full version.
This track marked BONNIE PINK’s first Top 10 entry on the Oricon charts in approximately six years and nine months, becoming a major hit with over 200,000 copies sold.
Easy to sing at karaoke and familiar to a wide range of age groups, it’s a safe choice even for gatherings with bosses or clients.
Bridge of Gloryyuzu
Eikou no Kakehashi (Bridge of Glory) is Yuzu’s 21st single, which became a hit in 2004.
It’s a classic that was also used as the theme song for the Athens Olympics.
The lyrics are very positive and carry a message that encourages those who are striving.
It’s a song that brings a tear to your eye as it recalls all the hard work—perfect for singing as a send-off at farewell parties or when everyone is united and working together on a project.