Is Twenty 1 a good place to start with Chicago?

Yes, Twenty 1 is recommended as a starting point for new Chicago listeners. A polished blend of adult contemporary and soft rock, layered with jazzy instrumentation and emotive vocals that evoke deep feelings. Released on January 29, 1991, Twenty 1 marked Chicago's return after a three-year hiatus following their album Chicago 18. This album emerged during a period when the band was negotiating its identity in the changing musical landscape of the early '90s, balancing their established soft rock sound with contemporary influences.

Twenty 1 works well if you're into steady mid-tempo listening experience, smooth melodies for relaxation and rich harmonies for evening ambiance.

How many songs are on Twenty 1?

Twenty 1 has 12 tracks, running approximately 52 minutes.

Twenty 1

Chicago · 1991

52 min · 12 tracks · jazz

A polished blend of adult contemporary and soft rock, layered with jazzy instrumentation and emotive vocals that evoke deep feelings.

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Top tracks — play these first

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Explain It to My Heart Start here — This opening track sets the tone for the album with its heartfelt lyrics and smooth melodies, showcasing the band's signature sound and emotional depth.
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What Does It Take — An exploration of longing and vulnerability, this song exemplifies Chicago's ability to fuse pop sensibilities with jazz-influenced arrangements, making it a standout moment.
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Chasin’ the Wind — This track combines reflective lyrics with an uplifting melody, capturing the essence of hope and resilience that permeates throughout the album.

Elevation

Our rating, out of 100 — and why.

AI-generated from five scored dimensions. An opinion, not a measurement.

46 /100

Foothills

Higher than 10% of albums we've rated

The album blends polished adult contemporary with jazz elements, showcasing solid musicianship but lacking standout compositions.

What we noticed

The first half of the album features a consistent mid-tempo groove, while the second half introduces more varied tempos and dynamics.
Several tracks include extended instrumental sections that showcase the band's musicianship, particularly in brass and keyboard arrangements.
The album's final track ends with a gradual fade-out, creating a sense of closure after the preceding emotional intensity.

Composition 25% of the score: 6/10
Craft 20% of the score: 7/10
Durability 25% of the score: 5/10
Distinctiveness 18% of the score: 5/10
Sequencing 12% of the score: 6/10

Influence 2/10

Little footprint beyond its audience. Reported but not counted — how far a record travelled describes its reception rather than the record, and a newer release has had less time to travel than an older one.

Is this for you?

Good fit if you like

steady mid-tempo listening experience
smooth melodies for relaxation
rich harmonies for evening ambiance
thoughtful reflections during quiet moments

Maybe skip if you

seeking high-energy tracks
prefer short, standalone songs

Where this album fits

In the catalog: Deep Cut — A solid entry that showcases Chicago's style but isn't a primary highlight in their catalog.
Themes: smooth jazz landscapes· emotive love stories· early '90s nostalgia
Career context: Released on January 29, 1991, Twenty 1 marked Chicago's return after a three-year hiatus following their album Chicago 18. This album emerged during a period when the band was negotiating its identity in the changing musical landscape of the early '90s, balancing their established soft rock sound with contemporary influences.
Stylistic neighbors: Earth, Wind & Fire· Steely Dan· Blood, Sweat & Tears

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Moments worth listening for

Where the writing does something specific.

What Does It Take

The narrative shifts from questioning love's complexities to expressing raw yearning, revealing deeper emotional layers as it unfolds.

The progression from inquiry to vulnerability illustrates a nuanced exploration of romantic uncertainty, showcasing the lyrical depth that characterizes much of the album.