[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, reliable songs that won’t miss the mark at company karaoke with your boss or for client entertainment (81–90)
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.
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?
Bitter VacationMrs. GREEN APPLE
When it comes to Mrs.
GREEN APPLE’s songs, many people probably think of melodies with a wide vocal range backed by vocalist Motoki Omori’s overwhelming singing ability, and may have given up on trying them at karaoke because they seem difficult.
For those people, I recommend the song Bitter Vacation, released in November 2024.
Among Mrs.
GREEN APPLE’s tracks, its melody line is relatively low in pitch and not overly complex, making it the kind of song you can sing comfortably along to its lively rhythm.
There are moments where a touch of irregular meter slips in, but once you get used to it, it’s not that hard—so be sure to add it to your karaoke repertoire.
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.