From Showa-era kayōkyoku to pop: songs that sound cool when you can really sing them
Many of you probably want to sing cool, deep tracks at karaoke with style.
In particular, Showa-era kayōkyoku and New Music, as well as early-to-mid Heisei J-POP, are packed with timeless masterpieces that still sound fresh decades after their release—a real treasure trove of cool, mature songs.
It’s precisely because of that universal appeal that these songs continue to be sung by today’s younger generation.
In this article, I’ll introduce plenty of those songs that, if you can pull them off, will give you that sophisticated edge.
I’ve picked selections mainly from Japanese music of the ’70s through the ’90s, with some of the latest J-POP mixed in, so use this as a reference when choosing songs for karaoke!
- A collection of nostalgic hits from the ’70s to 2000s that are perfect for livening up karaoke
- [For Men] Cool, Popular Songs That Impress at Karaoke
- Easy-to-sing karaoke songs recommended for men in their 50s
- Classic Showa-era songs that are easy to sing at karaoke
- Karaoke songs for men in their 40s: a curated selection of hit tracks women want to hear!
- A lineup of classics! Easy-to-sing Heisei-era songs, perfect for karaoke picks
- [For Men in Their 40s] A Collection of Songs That Score High at Karaoke [2025]
- Karaoke songs popular with women that they want men to sing
- [2025] Songs I Want to Try Singing at Karaoke! A Roundup of Popular Showa-Era Kayōkyoku
- Even karaoke beginners can relax! Easy-to-sing songs for men
- [Popular and Crowd-Pleasing!] Stylish Song Selections and Karaoke Tracks
- A lineup of classic hits! Karaoke songs recommended for the yutori generation
- [50s] Karaoke Popularity Rankings by Generation [2025]
From Showa Kayō to Pop: Cool Songs to Master (91–100)
Is it okay if I cry?Takajin Yashiki

Takajin Yashiki, a singer who gained great popularity in Osaka.
Anyone from Kansai probably knows him.
While he’s famous as a singer skilled at expressing women’s feelings, he actually released songs that convey men’s emotions as well.
One of them is “Naite mo Ii ka” (“Is It Okay If I Cry?”).
It candidly portrays male vulnerability, yet within that weakness you catch glimpses of a cool, mature edge.
The melody is also crafted to be both sweet and richly seasoned, so I encourage you to give it a try.
It's a sad color, isn't it?Masaki Ueda

Singer-songwriter Masaki Ueda is well known for his signature song “Kanashii Iro Yane – OSAKA BAY BLUES.” Initially, it seems only the latter subtitle was used, but the current title was adopted to better convey the song’s message.
The lyrics depict a sad romance set in Osaka.
Blending words that will resonate with anyone familiar with the city, it portrays a woman’s feelings in Kansai dialect.
Overall, though, it leaves a cool, mature impression.
The vocal style has a soulful vibe, so try singing it with strength and power.
hairy chestHideki Saijo
This is the 44th single by Hideki Saijo, a top idol singer who dominated the 1970s as one of the “New Big Three.” Written and produced by singer-songwriter Yoshinori Monta, the song features a catchy melody over a funky ensemble and is recognized across generations.
Its arrangement makes it easy to add call-and-response shouts, so it’s perfect for getting everyone hyped at karaoke.
With its brisk, ever-changing structure, it’s a cool, quintessential Showa-era classic.
Do whatever the hell you want.Kenji Sawada
Known by his nickname “Julie,” singer Kenji Sawada’s 19th single thrilled fans with his sexy vocals and looks.
With its catchy melody and rock-influenced arrangement, the song became a major hit, and it drew attention again in 2003 when B’z guitarist Tak Matsumoto included a cover on his album, featuring vocals by B’z singer Koshi Inaba.
The lyrics, depicting a man’s feelings toward his lover, evoke a complicated mix of bold decisiveness and lingering vulnerability—an emotion that’s hard to neatly resolve.
Beloved by a wide range of listeners, it’s the kind of number that’s guaranteed to hype up any karaoke setting.
Pink sighMariko Takahashi

In addition to being cool and chic, why not try singing “Momoiro Toiki,” which also creates a mature vibe? This song was released by Mariko Takahashi in 1984.
Set to an exotic melody, it expresses the romantic feelings of an adult woman.
By the way, the title “Momoiro Toiki” refers to the sigh of a woman in love.
If you listen closely, you can hear parts in the song that are sung almost like sighs.
The trick is to imitate that style a bit more exaggeratedly than usual.
triggerMasayuki Sera

This is the third single by the rock band Masanori Sera & Twist, formed around Masanori Sera, which helped make the then-still-uncommon genre of rock popular in the J-POP scene.
The arrangement, featuring gritty vocals and a Hammond organ sound, has a cool vibe that truly evokes Western rock.
With its blend of wistful atmosphere and aggressive energy, it’s guaranteed to hype up any karaoke session.
It’s a timeless classic that lets not only those who lived through its era but also younger singers project a cool, mature edge.
In conclusion
Focusing on Showa-era kayōkyoku and J‑POP up through the ’90s, we’ve introduced a rich selection of songs that have a cool, mature vibe when you can sing them well.
We’ve picked only timeless classics we’d recommend not just to those who listened in real time back then, but also to today’s younger generation.
If you ever feel like singing something different at karaoke or want to nail it with a golden oldie, we hope you’ll use this article as a guide for choosing your setlist.








