How to Dress Well’s 2010 “I Wish” Cover Put Love Remains in Close-Up

The surviving record of a close-up cover

On September 27, 2010, a short film placed Tom Krell almost uncomfortably close to the camera. Performing as How to Dress Well, he covered R. Kelly’s “I Wish” during a Chicago session for the video project Yours Truly. The clip carried its own title, “Waking Up to Life Sometimes Seems Worse.” A contemporary Pitchfork report described it as dark, tightly framed and especially suited to Krell’s fragile falsetto.

That report is the most dependable surviving public account of the film. Its details matter because they distinguish the session from the many unofficial recordings and mislabeled uploads that can accumulate around a cover song. This was not merely How to Dress Well performing “I Wish” somewhere in 2010: it was a filmed Yours Truly session made in Chicago and circulated under a separate title.

The timing was unusually revealing. Krell had told Dummy earlier that month that his debut album, Love Remains, would arrive through Lefse on September 21. The same September 2 interview presented 2010 as a breakthrough year involving two seven-inch releases, the album and more free music planned for his blog. Pitchfork reviewed the record on September 24, three days before reporting the cover. Rather than previewing a distant release, the session appeared as listeners were beginning to understand what the new album was doing.

Why “I Wish” fit the project

“I Wish” was a recognizable turn-of-the-century R&B single rather than an obscure selection used to demonstrate specialist taste. The Official Charts Company’s archive records its first UK chart appearance on October 21, 2000, a No. 12 peak on the main singles chart and a No. 1 peak on the organization’s hip-hop and R&B chart. A decade later, its melody and backward-looking emotional premise offered Krell something immediately legible to transform.

That choice is important. A cover can function as easy online currency: the established title supplies recognition, while the younger performer receives credit for an unexpected arrangement. Krell’s performance instead belonged to a project already organized around the imperfect recollection of R&B. Familiarity was not a marketing shortcut attached to the music; it was part of the music’s subject.

The source song’s polished construction placed it at a productive distance from How to Dress Well’s early recordings. Krell worked with falsetto, slow-jam contours and layered voices, but presented them through hiss, clipping, heavy reverb and rhythms that seemed to come from another room. The Yours Truly film’s darkness and extreme proximity offered a visual counterpart to that approach. Its camera apparently reduced the distance to the singer even as the sound world associated with How to Dress Well made songs feel worn, obscured or only partly recoverable.

The alternate title, “Waking Up to Life Sometimes Seems Worse,” deepened that tension without turning the performance into a different composition. It framed the cover as an encounter with waking, memory and emotional discomfort. Crucially, the selection was not presented as kitsch or as a joke about mainstream R&B. The seriousness of “I Wish” was the foundation on which Krell’s interpretation depended.

From free EPs to Love Remains

How to Dress Well had emerged through accumulation rather than a conventional introductory campaign. According to Pitchfork’s September 24 review, the project began posting music in autumn 2009 with the free EP The Eternal Love, followed by roughly half a dozen more EPs within six months. At first the recordings arrived with little biographical explanation. They were eventually identified as the work of Krell, then a philosophy student dividing his time between Brooklyn and Cologne.

A later, detailed FADER profile corroborated the broader shape of that period: Krell recorded seven self-issued EPs over about eight months while studying in Germany, and much of their material became the raw material for Love Remains. The album therefore did not erase the project’s online beginnings. It gathered, revised and sequenced them into a full-length statement.

The official How to Dress Well Bandcamp edition preserves the album’s 14-song sequence, beginning with “You Hold the Water” and closing with “Suicide Dream 1.” Between them are “Ready for the World,” “My Body,” “Can’t See My Own Face,” “Endless Rain” and “Decisions.” Although that page documents Domino’s later 2017 edition rather than the original Lefse release date, its track list agrees with the 14-track, approximately 39-minute album catalogued by AllMusic.

Those titles reveal how consistently the record returns to bodies, absence, water and mortality. They do not operate as a literal explanation of the Yours Truly cover, but they show why “I Wish” could enter the same emotional space without seeming like a novelty. Krell was drawn to songs whose direct melodic feeling could remain perceptible after their surfaces had been distressed.

R&B remembered through damaged sound

Contemporary critics heard that distress as structural rather than accidental. Pitchfork described Love Remains as a ghosted version of the late-1980s and 1990s R&B Krell loved, with sound altered by the processes of memory. Its review singled out “Ready for the World,” a partial reworking of the 1986 slow jam “Love You Down,” as a concise example: lyrics blur, percussion becomes difficult to locate and the vocal melody survives more clearly than the words carrying it.

That precedent makes the “I Wish” cover central to an understanding of How to Dress Well. Krell was already placing existing R&B inside recordings concerned with distance and partial recognition. The cover extended that method from an album track into a filmed performance whose source could be named immediately. Listeners did not have to identify a faint allusion; the act of transformation was placed in front of them.

The effect should not be reduced to the label “lo-fi R&B.” Low fidelity describes the surface but not the full purpose. Hiss, overload and indistinct words allowed Krell to separate emotional communication from complete information. A listener might fail to make out a sentence while still hearing yearning in a falsetto’s rise or strain. The A.V. Club’s review similarly characterized the album as an exploration of feelings fading over time, built from fragmentary beats, ambient drones, reverberant piano and multitracked vocals.

AllMusic later emphasized the same connection between recording quality and recollection. Its review notes that the album regularly hisses, clips and exceeds clean recording levels, while arguing that those qualities evoke memories, dreams and impressions. That critical agreement is useful because it prevents the cover from being mistaken for an isolated genre exercise. “I Wish” belongs to a sustained investigation of what happens when a song remains emotionally vivid after its sonic details begin to decay.

What the camera added

The surviving description suggests that the Yours Truly film translated this method without simply illustrating it. A dark, super-close frame removes the anonymity that had surrounded the earliest EPs: there is a face, a body and a visible act of singing. Yet proximity does not necessarily produce conventional clarity. At close range, breath, effort and hesitation can become more conspicuous, making the performance feel less polished rather than more complete.

That distinction helps explain why the cover could carry its own title. “Waking Up to Life Sometimes Seems Worse” identifies the clip as a particular performance and atmosphere, not merely a substitute recording of “I Wish.” The familiar song supplies a durable melodic structure; Krell and the filmmakers change the room around it. The performance becomes an argument that intimacy can arise from compression, darkness and vulnerability rather than pristine sound.

The Chicago setting also belongs to the documented history rather than decorative mythology. Pitchfork explicitly located the session there. Later interviews would establish that Krell moved to Chicago during this period, but the film does not need to be treated as a grand statement about the city or its R&B lineage. Its scale is deliberately smaller: one singer, an inherited song and a camera close enough to make the act of reinterpretation the event.

A compact key to an unusual debut

A single web session did not create the How to Dress Well aesthetic. By September 2010, Krell had already spent a year releasing, revising and sequencing music, and Love Remains offered the fuller statement. What the “I Wish” film supplied was concentration. It brought the project’s principal elements—R&B memory, falsetto, damaged intimacy and emotional directness—into one readily understood encounter.

The cover also demonstrated the difference between treating R&B as a collection of stylish signifiers and treating its songs as serious emotional structures. Krell did not need to reproduce the original record’s scale to acknowledge its force. He could strip away polish, place the singer in darkness and leave the melody carrying the weight.

That is why the session remains more than a minor curiosity adjacent to Love Remains. It shows, in miniature, how How to Dress Well could draw a song out of public repertoire and make it feel private without denying where it came from. The recognizable composition and the obscured presentation do not cancel each other. Their friction is the point: a song remembered clearly enough to sing, but transformed by the distance through which it returns.