[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)
threadMiyuki Nakajima
If you want to sing something gently in a calm setting, I recommend Miyuki Nakajima’s “Ito” (Thread).
It’s a tender song about family love and the ties between people.
Since its release in 1998, it has remained a beloved classic and has been covered by many artists.
It was also the theme song for the drama “Seija no Koshin” (March of the Saints), so those who watched the show might feel nostalgic and be reminded of that time.
A Cruel Angel's ThesisYoko Takahashi
A song by female singer Yoko Takahashi that gained explosive support as the theme song for the TV anime Neon Genesis Evangelion.
Despite being an anime song, it consistently ranks among the most popular karaoke tracks, and the many cover versions by various artists attest to its wide recognition and enduring popularity.
It’s a karaoke staple sung across generations, so it’s a safe choice that won’t miss even when singing with older supervisors or clients—an upbeat crowd-pleaser for any occasion.
Que sera, seraMrs. GREEN APPLE
Mrs.
GREEN APPLE’s songs, which portray the courage to face life’s hardships with a positive outlook, resonate deeply with listeners.
The phrase “que sera sera,” meaning “what will be, will be,” is especially memorable, and the lyrics are characterized by a sense of hope for the future.
Released in April 2023, this song was also chosen as a TV drama’s theme, winning broad sympathy.
Its bright melody—enjoyable across generations—and highly relatable, message-driven lyrics are its main appeal.
It’s a safe pick for karaoke at workplace gatherings or dinners with clients, where people of various ages come together.
TRUE LOVEFumiya Fujii
Characterized by a poignant melody that resonates with the heart and bittersweet lyrics, this work was released in November 1993 and was used as the theme song for the Fuji TV drama “Asunaro Hakusho.” As Fumiya Fujii’s solo debut single, it holds an important place in his musical career.
The lyrics, which depict conflict and regret in love as well as gratitude toward a past partner, struck a chord with many listeners.
It is also a popular choice as a wedding standard, and in 1995, there was even a TV program auction where the right for Fujii to sing this song at a wedding reception was sold for over one million yen.
It’s also a safe, widely accepted pick for karaoke with bosses or clients, appealing to a broad range of ages.
Get WildTM NETWORK
This song, with its urban sound reminiscent of an ’80s night in the city, has long been cherished as one of TM NETWORK’s signature tracks.
Released in 1987, it’s also known as the ending theme of the anime City Hunter and remains a staple favorite at karaoke.
The innovative, synthesizer-driven sound paired perfectly with Takashi Utsunomiya’s powerful vocals has captivated listeners across generations.
Choosing this song to wrap up a drinking party with your boss or clients will instantly lift the mood.
With its familiar melody and singability, it’s an ideal pick to energize any karaoke gathering.
Timing ~タイミング~Black Biscuits
This song, themed around the importance of timing in everyday life, portrays miscommunications and daily frustrations.
Released on April 22, 1998, it became a major hit, reaching No.
2 on the Oricon charts.
It achieved the highest sales among songs by units born from the variety show “Ucchan Nanchan no Urinari!!”.
The piece is loved across generations for its catchy melody and relatable lyrics.
It’s likely to be appreciated even in business entertainment settings with bosses or clients, as a song that can be enjoyed across age groups.
It’s also expected to lighten the mood when sung at karaoke thanks to its ease of singing and familiarity.
TOMORROWMayo Okamoto
Mayo Okamoto’s debut song carries a powerful message.
Its lyrics give you the courage to overcome hardships, and her gentle, embracing voice resonates deeply.
Released in May 1995 and used as a TV drama theme, the song became a massive hit, selling over two million copies.
Since then, it has continued to inspire hope and courage—sung with children in areas affected by earthquakes, among many other occasions.
It’s perfect for times when you’re struggling in life or want to encourage someone dear to you.
Sing it at karaoke with your boss or clients, and it’s sure to spark empathy across generations.