[2026] Smooth sailing at karaoke and work! Safe, reliable songs that won’t miss the mark for company bosses and business entertainment karaoke
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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[2026] Smooth sailing at karaoke and work! Safe, foolproof songs you can't go wrong with for karaoke with your boss or at business entertainment (71–80)
Voice of the Seaurashima tarou
A song by Kenta Kiritani, the actor who plays Urashima Taro in au’s “Santaro Series” commercials.
Because it became popular as a commercial jingle, many people across generations will likely recognize it.
With an Okinawan-inspired melody and the sound of the sanshin, it’s arranged to be pleasant for listeners of any age, making it a foolproof choice for karaoke with older bosses or clients.
The key is low and the melody is simple, so if you know the song, you can handle it even if you’re suddenly asked to sing.
240 Million EyesGō Hiromi
The 50th single by Hiromi Go, a male singer who also thrived as an actor and TV personality and enjoyed immense popularity as one of the “New Big Three.” With its instantly recognizable, impactful lyrics and melody, it’s truly a karaoke classic.
When you actually try singing it, the melody rises and falls dramatically, so it takes practice to pull off.
But if you can sing and dance to it—especially at karaoke with a boss in their 50s—it’s a guaranteed crowd-pleaser.
Why not practice and make it your own?
Fortune Cookie in LoveAKB48
This AKB48 release captivates with its exhilarating disco-style sound and uplifting message.
The lyrics are memorable for celebrating a spirit of moving forward—believing in a bright future despite romantic missteps and everyday setbacks.
Released in August 2013, the track features Rino Sashihara as center, with lyrics by Yasushi Akimoto.
It has been used across various media and has won multiple awards.
It’s an essential pick for karaoke with your boss or clients, guaranteed to liven up the atmosphere with its universally loved melody and easy-to-learn chorus choreography.
[2026] Smooth sailing at karaoke and work! Safe, reliable songs that won’t miss the mark at company karaoke with your boss or for client entertainment (81–90)
TouchIwasaki Yoshimi
This song, still beloved as a classic from the Showa era, was released in September 1985 as the theme song for the anime Touch.
Its lyrics delicately portray feelings of love and heartbreak, and it’s characterized by a memorable guitar intro.
The phrases capturing the bittersweet emotions of youth really hit home.
Yoshimi Iwasaki’s clear, translucent vocals further enhance the song’s world, making it a track that can be enjoyed across generations.
Sing it together, and it’s sure to lift the mood of any gathering in an instant.
Crossing Amagi PassIshikawa Sayuri
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?
Tears aren’t just for show.Nakamori Akina
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.
I’ve always liked you.Saitō Kazuyoshi
A heartwarming love song that gently sings about feelings for a first love.
Sparked by a reunion at a school alumni gathering, its lyrics—openly expressing long-held feelings—have resonated with many.
Released in April 2010, the song also drew attention as a Shiseido commercial tune.
The music video, inspired by the Beatles’ Rooftop Concert, was reportedly filmed in Utsunomiya, the hometown of Kazuyoshi Saito.
It’s a perfect track for when you want to bask in nostalgia or convey your feelings to someone special.
Sing it at karaoke, and it’s sure to warm the room across generations.