The 1990s File Feature
This & That
This That by Michael Penn: Literate Rock for a New Decade Picture the dawn of the 1990s, when alternative and singer-songwriter rock was beginning to reasser…
01 The Story
"This & That" by Michael Penn: Literate Rock for a New Decade
Picture the dawn of the 1990s, when alternative and singer-songwriter rock was beginning to reassert itself after the gloss of the previous decade, and listeners were hungry for music with intelligence and substance. Into that moment stepped Michael Penn, a thoughtful, literate songwriter whose intricate craft set him apart from the pack. Following the breakthrough of his biggest hit, he offered "This & That," a sharp, melodic single that showcased his gift for clever wordplay and richly textured rock.
A Songwriter of Substance
Michael Penn arrived as a singer-songwriter of unusual depth, a craftsman whose music prized wit, melody, and lyrical intelligence. He had broken through at the very end of the 1980s with a major hit, establishing himself as a fresh and distinctive voice. "This & That" came from that same successful period, building on his momentum as he sought to prove that his appeal extended beyond a single song. It was the work of an artist confident in his literate, melodic approach.
The early 1990s were a transitional time in rock, with the polished sounds of the 1980s giving way to grittier, more substantive music. Penn fit naturally into this shift, offering songs that valued craft and meaning over spectacle. His thoughtful, jangly rock connected with listeners and critics who appreciated intelligence in their pop music, positioning him among the more respected songwriters of the era's emerging landscape.
Crafted and Melodic
Musically, the song reflects Penn's gift for combining sturdy melody with intricate songcraft. The arrangement is built around jangly guitars and a strong sense of melodic structure, framing his distinctive vocal and clever lyrics. There is a literate, slightly wry quality to the recording, the sound of a songwriter who treats his craft seriously without taking himself too seriously. It is intelligent pop-rock made with evident care.
What distinguishes the song is the balance Penn strikes between accessibility and depth. The melody is immediate and engaging, while the lyrics reward closer attention with their wit and observation. This was music that worked on first listen but revealed more with repeated plays, the mark of a songwriter who respected his audience's intelligence. That combination of hooks and substance defined Penn's appeal throughout this period.
A Modest Chart Run
On the Hot 100, the single performed modestly. "This & That" debuted on April 28, 1990, entering at number 90, and it climbed steadily through May. By mid-month it had reached the low 70s, and it continued to rise. The single peaked at number 53 on May 26, 1990, a respectable showing that confirmed Penn's continued presence on the chart. It spent eight weeks on the Hot 100 during its run.
A peak of number 53 placed the song in the middle tier of the chart, a solid follow-up showing for an artist whose appeal leaned toward the discerning rather than the mass market. For Michael Penn, the result reflected his standing as a respected, critically admired songwriter rather than a chart-topping pop star. The single kept his name in circulation and reinforced his reputation as a craftsman of literate, melodic rock.
A Songwriter's Songwriter
In the larger story of Michael Penn's career, "This & That" stands as a strong example of his intelligent, melodic approach, a single that captured the qualities that earned him lasting critical respect. While he never became a massive commercial force, he built a devoted following among listeners who valued craft and substance. The song remains a fine representation of his particular gifts.
For fans of literate, melodic rock and discerning songwriting, the recording is a genuine reward. Put it on, and you will hear an artist who prized intelligence and craft, delivering a sharp, tuneful single that respects both the melody and the mind. Penn's work endures precisely because of that commitment to substance, and this song captures it admirably.
"This & That" — Michael Penn's singular moment on the 1990s charts.
02 Song Meaning
The Meaning Behind "This & That" by Michael Penn
True to Michael Penn's reputation as a literate songwriter, "This & That" carries a meaning shaped by wit, observation, and emotional nuance. The song explores the complexities of a relationship and the often contradictory feelings that accompany human connection. Its title itself suggests ambivalence and the scattered, hard-to-pin-down nature of the emotions it examines.
The Complexity of Connection
At its core, the song reflects on the tangled, often contradictory feelings that arise in relationships. Rather than offering simple declarations of love or heartbreak, it dwells in the messier emotional middle ground. The song embraces ambivalence and emotional complexity, capturing the way real feelings rarely fit neat categories. That willingness to explore nuance distinguishes it from more straightforward pop songs about love.
Wit and Wordplay
Penn's gift for clever language is central to the song's meaning. The lyrics use wordplay and sharp observation to convey emotional truths that resist simple statement. The song uses wit to illuminate genuine feeling, finding ways to express complicated emotions through intelligence and craft rather than sentimentality. That literate approach invites the listener to think as well as feel, rewarding attention with deeper understanding.
This intelligence reflected Penn's broader artistic identity. His writing treated the listener as a thoughtful equal, trusting them to appreciate subtlety and nuance. That respect for the audience gave his songs a distinctive depth, setting them apart from music that aimed only for immediate emotional impact.
Ambivalence as Honesty
The song's embrace of mixed feelings carries its own kind of honesty. By refusing to simplify the emotional reality of relationships, it offers a more truthful portrait of how people actually feel. The song finds truth in emotional ambiguity, acknowledging that connection is rarely clear-cut or easily resolved. That honesty resonated with listeners who recognized their own complicated experiences in the lyric.
This refusal of easy answers fit the early-1990s appetite for substance and authenticity. As pop music shifted toward greater emotional realism, Penn's nuanced approach felt timely, offering a vision of relationships grounded in genuine complexity rather than romantic cliche. Listeners weary of empty sentiment found something refreshing in a songwriter willing to admit that feelings are tangled and rarely tidy.
Intelligence as Emotional Care
There is a quiet tenderness in the way the song treats its subject, despite its wit. Penn's cleverness never becomes cold or distancing; instead, it serves the emotion, finding precise language for feelings that simpler songs would flatten. The song proves that intelligence and feeling can coexist, demonstrating that careful craft can deepen rather than diminish emotional impact. That marriage of head and heart defined Penn's appeal, and it gives the song a warmth that endures beneath its sharp surface.
A Thoughtful Resonance
Decades on, the meaning of "This & That" remains as thoughtful and rewarding as ever. It is a song about the complicated, contradictory feelings of human connection, delivered with the wit and intelligence that defined Michael Penn's craft. Press play, and you will find a songwriter who trusted his listeners to engage with emotional nuance, a reminder that the most rewarding songs are often those that embrace life's complexity rather than reducing it to simple sentiment.
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