1. Hess
Fortune 500 Rank: No. 394
Drop in rank: 253 spots

Hess Corporation (HES) has toppled from last year’s perch at No. 141 to No. 394. Although the oil and gas giant sold its retail arm—including 1,256 gas stations—to Marathon Petroleum in 2014, corporate streamlining hasn’t fully insulated the company from falling oil prices. Last year, Hess posted a net loss of $1.1 billion in addition to a 69% decline in revenue.

2. Marathon Oil
Fortune 500 Rank: No. 438
Fall in rank: 211 spots

As oil prices spiraled, the energy giant fell to No. 438 from No. 227 in 2014. Last year, Marathon (MRO) worked to minimize costs, slashing year-over-year production expenses by 24% and cutting their workforce by over 20%. Still, the global oil glut has taken a steep toll on the company’s sales, with profits plummeting 172%.

3. Apache
Fortune 500 Rank: No. 388
Fall in rank: 170

In an effort to pare its operations last year, Apache (APA) slashed expenses by 60% and reduced its 126-rig count in 2014 to 34. Nonetheless, this Houston-based oil and gas company reported $23 billion in losses. Year-over-year revenue for the company also plunged to $6.7 billion from $12.7 billion in 2014.

4. Anadarko
Fortune 500 Rank: No. 324
Fall in rank: 162

Headquartered in The Woodslands, Texas, Anadarko (APC) reported a net loss of $1.25 billion last year, despite trimming its spending by almost 40%. Revenue also shrank 53% to $8.7 billion, pushing the company 162 notches back down the list to No. 324.

5. EOG Resources
Fortune 500 Rank: No. 322
Fall in rank: 155

2015 was the first time in history that EOG Resources (EOG)—spun off from Enron in 1999—found itself in the red. Headquartered in Houston, the oil and gas company reported a 51% decline in revenue last year, as well as $4.5 billion in losses.

6. eBay
Fortune 500 Rank: No. 300
Fall in rank: 128

Although the e-commerce giant reported 5% growth in its active buyer base last year, eBay’s (EBAY) decision to spin off Paypal last July has taken a substantial bite out of its revenue. Sales declined 47% last year, dragging the San Jose e-commerce giant down to No. 300 on the list. (Meanwhile, Paypal (PYPL) has debuted on the Fortune 500 in its first year of freedom—ranking just 7 spots behind its ex-parent.)

7. Visteon
Fortune 500 Rank: No. 470
Fall in rank: 126

Formerly a Ford company, Visteon (VC) went bankrupt and emerged in 2010. But it’s not all bad news—since its stock’s 2012 lows, shares have climbed some 160%. It’s also a smaller company than it once was. Formerly a broad provider of auto accoutrements, it’s shed businesses like interiors and climate control to focus on cockpit electronics. And in a world with increasingly wired car displays, that market is expected to hit $52 billion by 2020. If Visteon goes on to capture a larger a fraction of that, it could end up significantly higher on the 500 list in future years.

8. Oneok
Fortune 500 Rank: No. 348
Fall in rank: 111

ONEOK (pronounced “one-oak”) (OKE) dropped from No. 237 to No. 348 after sustaining a 40% decline in revenue. That’s largely owing to the downturn in gas prices—as well as a spate of ice storms in the mid-continent last winter, which tacked on an extra $4 million in expenses. The Tulsa-based energy firm also saw a 22% decline in profits.

9. Occidental Petroleum
Fortune 500 Rank: No. 225
Fall in rank: 110

This Houston-based oil and gas behemoth reported a quadruple-digit profit percentage change last year. Although Occidental’s (OXY) reduced its drilling activity by 30% in a bid to offset the global slump in oil prices, the company reported a -1,371% year-over-year change in profit, sustaining losses of $7.8 billion—the largest since the company debuted on the Fortune 500.

10. Ashland
Fortune 500 Rank: No. 473
Fall in rank: 101

While the energy giants of the Fortune 500 have fought hard against nose-diving oil prices only to see their revenues fall by 50%, Ashland (ASH) announced its intentions last September to voluntarily divide itself in half. This Kentucky-based chemicals company—maker of Valvoline motor lubricants (which has famously fueled NASCAR teams)—is seeking to divest itself of its motor oil business and focus on producing speciality chemicals.