Synonym: bankrupt, destitute, down-and-out, poor. Similar words: openness, pitiless, guileless, merciless, mercilessly, funnily, tennis, kenning. Meaning: ['penɪlɪs] 
adj. not having enough money to pay for necessities.
adj. not having enough money to pay for necessities. 
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31. Uncle Charlie was also with us now, and Uncle Charlie was jobless and penniless.
32. He had gone from being a penniless student to become a multimillionaire.
33. I don't want to go down in history as a great songwriter because I died penniless.
34. And yesterday Eva, who had poured her life savings into the six-bedroom house,(http://sentencedict.com/penniless.html) was left devastated and penniless.
35. I was left stranded penniless in a strange city.
36. By then he was a penniless, eccentric loner.
37. The penniless man had to bum a ride home.
38. In the backside, there is a penniless heavy haversack , but your back is straight, your footstep is flimsy, your corners of the mouth smile is haughty and fortitude.
39. A penniless Dickens married Catherine Hogarth in 1836 and she bore him 10 children before he threw her out in 1858, banishing her from her children, as he took up with another woman.
40. Actually many famous movie stars begin with tiny and penniless walk-on.
41. The Social Security Retirement Program is made up of two trust funds, the larger of which could go penniless by next year.
42. If he carries on drinking like that, he'll land up jobless and penniless.
43. Masterless, penniless, and with my only means of livelihood, fighting, gone, I determined to work my way to the southwest and attempt to retrieve my fallen fortunes in a search for gold.
44. He moved to New York and performed an untraditional roster of penniless actor jobs – yoga instructor, manure shoveller, railroad-loader.
45. In the novels of the period the dilemma was felicitously solved by the discovery, on the last page, that the apparently penniless heroine was really a great heiress.
46. He was an old emigre gentleman, blind and penniless, who was playing his flute in his attic, in order to pass the time.
47. If the breadwinner deserts the family, it will be left penniless.
More similar words: openness, pitiless, guileless, merciless, mercilessly, funnily, tennis, kenning, perennial, biennial, millennia, senile, table tennis, centennial, millennium, juvenile, bicentennial, nile river, pen name, pennant, juvenile delinquent, juvenile delinquency, carelessness, uselessness, selflessness, tactlessness, recklessness, hopelessness, homelessness, faithlessness.