[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!
- Songs everyone knows across generations. A roundup of karaoke tracks anyone can sing, regardless of age.
- [2025] Classic Karaoke Songs That Hype Up Year-End and New Year Parties
- [For People in Their 40s] Ranking of Easy-to-Sing Karaoke Songs [2025]
- [Karaoke] A roundup of songs that are easy for women to sing!
- [Hit Songs] A Special Feature on Japanese Karaoke Tracks Recommended for Business Entertaining
- [For Men in Their 40s] A Collection of Songs That Score High at Karaoke [2025]
- [2025 Edition] Songs That Will Get the Crowd Going—Perfect for Women in Their 40s to Sing at Karaoke
- Recommended karaoke songs that will liven up a welcome party
- Recommended picks for karaoke! Easy-to-sing songs recommended for Gen Z
- A lineup of classics! Easy-to-sing Heisei-era songs, perfect for karaoke picks
- [2025] Liven Up Your Party! A Roundup of the Newest J‑Pop Hits and All-Time Crowd Favorites
- Even karaoke beginners can relax! Easy-to-sing songs for men
- [For Women in Their 40s] A Collection of Songs That Score High at Karaoke [2025]
[2025] Smooth sailing at karaoke and at work! Safe, reliable songs that won’t miss the mark for company bosses or client entertainment at karaoke (71–80)
Suddenly, SinbadSouthern All Stars
A classic of the Shonan sound that evokes the summers of youth.
Released in June 1978 as Southern All Stars’ debut single, it revolutionized Japan’s music scene.
Its buoyant feel rides on a 16-beat rhythm, paired with lyrics woven from uniquely chosen words.
The depiction of seaside romantic maneuvers tickles the listener’s heart.
The atmosphere that conjures summer beaches and youthful infatuation makes it perfect for mixers with bosses or clients, where it can spark cross-generational connections!
Effeminate; overly sentimental; being clingy/whiny (context-dependent)Golden Bomber
This song, which candidly portrays a bittersweet unrequited love, is Golden Bomber’s seventh single, released in October 2009.
Its unique sound, blending elements of Showa-era pop and Eurobeat, is a major draw.
The lyrics—said to be based on Sho Kiryuin’s real-life experience—vividly convey the clingy emotions of a heartbroken man.
Having won a JASRAC Award in 2013 and ranked highly on karaoke charts, the song has captured many hearts—and it’s perfect for karaoke with your boss or clients!
TouchYoshimi Iwasaki
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.
Kiss me right nowLINDBERG
It’s a classic with a powerful, pop-infused sound that really leaves an impression! Released in February 1990, this song is known as the theme for the Fuji TV drama “The One I Love Most in the World!” and became a massive hit, ranking third on the Oricon year-end singles chart that same year.
The lyrics vividly capture the pounding heart of someone in love with passionate imagery that truly resonates with listeners.
They express the sweetness and the bittersweet ache of romance, as well as its tension, making it easy for many people to relate.
It’s also a great choice for karaoke with bosses or clients—an enjoyable song across generations.
With its irresistibly catchy melody and universally relatable lyrics, it helps create a warm, friendly atmosphere and makes everyone want to sing along.
240 Million EyesHiromi Go
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?
SakurazakaMasaharu Fukuyama
This is Masaharu Fukuyama’s 15th single, and he is active across a wide range of fields as an actor and singer.
It’s a classic song that’s frequently sung at karaoke and widely known across generations.
With its beautiful melody and relaxed tempo, it’s easy to listen to, and if you’re unsure what to sing at karaoke with older bosses or clients, this fail-safe choice will draw everyone in.
When we think of difficult karaoke songs, high-pitched numbers often come to mind, but this one is quite low; if you’re not careful, it can be so low that your voice won’t carry.
Keep that in mind when you sing.
Chururi (feat. Takako Matsu)yuzu
Sung by Yuzu and Takako Matsu, this song is a heartwarming piece filled with nostalgia and bittersweet emotion.
The gentle vocals wrap around feelings of recalling the past in everyday life and longing for someone dear.
Released digitally in November 2024, it was featured in the Nissan Sakura commercial and drew attention for the trio’s collaboration on Fuji TV’s 2024 FNS Music Festival.
When you find yourself missing someone and feeling a pang of sorrow, give this song a listen—it will surely stay close to your heart.