[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 for karaoke and work! Safe, fail-proof songs that won’t miss at company karaoke with your boss or client entertainment (81–90)
ultra soulB’z
Characterized by an exhilarating melody and a memorable chorus, this song is loved by people of all ages.
Released in 2001, it’s one of B’z’s signature tracks, and its fiery call-and-response in the hook is perfect for creating a sense of unity at karaoke.
The lyrics, which convey a strong will to face adversity and a forward-looking energy, have the power to give listeners courage and hope.
Chosen as the official theme song for many FINA World Aquatics Championships, including Fukuoka 2001, this track helps you forget work fatigue and brightens the atmosphere, making it a safe pick even for business social gatherings with bosses or clients.
Crossing Amagi PassSayuri Ishikawa
Among enka classics, this is a true masterpiece.
If a new female employee confident in her karaoke skills takes it on, I think she’ll quickly win favor with her enka-loving boss! I recommend practicing it as a trump card.
Enka may seem old-fashioned, but once you sing it seriously, it’s actually a lot of fun.
These pop songs were originally made with karaoke in mind.
Why not give it a try—belt it out with strong vibrato and go for it?
Rainy BlueHidemasa Tokunaga
This song, which opens with a midnight scene at 12 a.
m.
, is Hideaki Tokunaga’s debut track, depicting loneliness and wistfulness in the rain.
It expresses the feeling of still being hung up on a love that should have ended, overlaying the rain’s blue-tinged imagery with the sadness and solitude it symbolizes.
Released in January 1986, it peaked at No.
90 on the Oricon chart.
As of August 2023, the official video on YouTube has surpassed 18 million views, and the song continues to be loved across generations.
It’s a recommended choice to close out a get-together with a wide age range or when you want to create a mellow, reflective atmosphere.
RunnerBakufū Slump
An anthem of encouragement for those who keep on running, sent out into the world by Bakufu Slump.
With lyrics that depict parting from friends, days of youth, and hope for the future, paired with a powerful melody, it resonates with many listeners.
Released in October 1988, the song was also performed at the 39th NHK Kōhaku Uta Gassen that same year and sold a total of 340,000 copies.
It has been featured on TV shows and in commercials, earning praise for its universal message.
Perfect for livening up a karaoke session or when you want to feel a sense of unity across generations!
Tears aren't just for show.Akina Nakamori
A signature hit from Akina Nakamori that represents the 1990s! Released in November 1984, this song was written and composed by singer-songwriter Yosui Inoue.
It topped the Oricon Weekly Singles Chart and ranked sixth on the year-end singles chart for 1985, becoming a massive hit with over 620,000 copies sold.
Singing about the transience of human relationships, loneliness, and the strength to be honest with one’s own feelings, this piece symbolizes Nakamori’s turning point from idol to artist.
With lyrics that resonate across generations and a beautiful melody, it’s perfect for singing at karaoke with your boss or clients.
Youthful AmigoShuji and Akira
Shuji and Akira’s songs are filled with friendship and youthful memories.
They’re characterized by fresh, sing-along melodies.
Released in November 2005, this track became a major hit as the theme song for the TV drama “Nobuta wo Produce.” It debuted at No.
1 on the Oricon chart and set a remarkable record with total sales exceeding 1.
62 million copies.
In karaoke, it’s popular as a song that can get everyone going, including bosses and clients.
It’s widely known across all ages and genders, and because it creates a friendly atmosphere, you can sing it with confidence even in business settings.
[2025] Smooth sailing at karaoke and work! Safe, crowd-pleasing songs you can’t go wrong with for company bosses and business karaoke (91–100)
FriendsREBECCA
It’s a memorable song with a beautiful, catchy melody and lyrics that invite empathy.
It skillfully portrays the delicate emotions wavering between friendship and romance, resonating with many listeners.
Released in October 1985, it was used as the ending theme for the NTV drama “Half Potato na Oretachi.” Widely recognized as one of REBECCA’s signature songs, it also marked a turning point for the band.
It’s a perfect choice when you’re unsure what to sing at karaoke.
Even with your boss or clients, it can help create a pleasant, relaxed atmosphere.
Its familiar melody is easy to sing and has made it a beloved song across generations.
In conclusion
I introduced safe, sure-fire karaoke songs that won’t miss when singing with colleagues or clients.
They’re all well-known across ages and genders, so they’re sure to get the crowd going without risk.
Also, if you stick with the artists mentioned in this article, other songs besides the ones listed here are great too—so try finding a track that’s comfortable for you to sing!